Substituted benzyl oximino compounds

ABSTRACT

The present invention relates to benzyloxyimino compounds of the formula I,where: R1 to R4, X, Y, and Z are as defined in the specification.

This is a 371 of PCT/EP98/01942 filed Apr. 2, 1998.

The present invention relates to benzyloxyimino compounds of the formulaI,

where:

X is N(COOCH₃)—OCH₃, C(COOCH₃)═CH—OCH₃, C(COOCH₃)═N—OCH₃,C(CONHCH₃)═N—OCH₃ or C(COOCH₃)═CH—CH₃;

Y is hydrogen, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxy;

Z is oxygen, C(R^(a))₂ or NR^(a), where

R^(a) is hydrogen or C₁-C₄-alkyl and, in the case of C(R^(a))₂, can beidentical or different;

R¹ is halogen, C₁-C₄-alkyl, C_(l)-C₄-haloalkyl or C₁-C₄-alkoxy;

R² is hydrogen, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or is phenyl with orwithout substitution by customary groups;

R³ is hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy;

R⁴ is C₁-C₄-alkyl or

phenyl with or without substitution by 1-3 substituents from thefollowing group: halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy or C(R^(b))═N—OR^(c), where

R^(b) is hydrogen or C₁-C₄-alkyl and

R^(c) is C₁-C₄-alkyl, C₃-C₄-alkenyl or C₃-C₄-alkynyl.

Additionally, the invention relates to processes and intermediates forpreparing the compounds I, to compositions and to the use of thecompounds I for controlling harmful fungi and animal pests.

Phenylcarbamates having a methoxyimino group in the ortho position aredisclosed in WO-A 93/15,046. α-Phenylacrylic acid andα-phenyl-α-methoxyiminoacetic acid derivatives having a methoxyiminogroup in the ortho position are known from EP-A 426 460, EP-A 460 575,EP-A 472 300, EP-A 585 751, WO-A 92/13,830, WO-A 92/18,487, WO-A92/18,494, JP-A 05/201,946 and JP-A 05/255,012. The compounds describedtherein carry a CH₂O—N═CR′R″ group in the position ortho to the groupcorresponding to X. The general definitions of the radicals R′ and R″include the definition of the radical R¹ in formula I and additionallyallow cycloalkyl and to some extent heterocyclyl substituents.

EP-A 463 488 and WO-A 90/07,493 disclose by way of exampleα-phenylacrylic acid and α-phenyl-α-methoxyiminoacetic acid derivativesin which the CH₂O—N═CR′R″ group carries alkyl and cyclopropyl, oxiranyl,or aziridinyl radicals as substituents R′ and R″.

The compounds described in the abovementioned publications are suitablefor use as crop protection agents against harmful fungi and to someextent against animal pests.

However, in many instances their activity is not satisfactory. It is anobject of the present invention, therefore, to provide compounds havingimproved activity.

We have found that this object is achieved by the substitutedbenzyloxyimino compounds of the formula I. Furthermore, we have foundintermediates and processes for preparing the compounds I, and the useof the compounds I and of compositions comprising them for controllingharmful fungi and animal pests. Preference is given to the fungicidalactivity.

The compounds of the formula I differ from the compounds disclosed inthe abovementioned publications EP-A 463 488 and WO-A 90/07,493 in thesubstitution of the methoxyimino group by the radical R⁴, which cannotbe hydrogen. In comparison to the known compounds, the compounds of theformula I have improved activity against harmful fungi and animal pests.

The compounds of the formula I can be obtained per se by the methodsdescribed in EP-A 463 488 and WO-A 90/07,493.

In particular, the compounds of the formula I in which Z is oxygen andC(R^(a))₂ are obtained by reacting an oxime of the formula II with abenzyl compound of the formula III.

In the formula III, L is a nucleophilically replaceable group, forexample halogen, such as fluorine, chlorine, bromine or iodine, inparticular chlorine or bromine, or alkyl- or arylsulfonates, such asmesylate or tosylate.

1. The reaction of the oxime II with the benzyl compound III is carriedout in a known manner at from −10° C. to 80° C., preferably 0° C. to 65°C., in an inert organic solvent in the presence of a base [cf. EP-A 463488].

In general, the reactants are reacted with one another in equimolaramounts. To improve the yield, it may be advantageous to employ anexcess of II, based on III.

The benzyl compounds of the formula III required for preparing thecompounds I are known from the literature [EP-A 420 091; EP-A 513 580;WO-A 93/15,046; WO-A 94/05,620] and can be prepared according to thecited literature.

The starting materials IIA required for preparing the compounds I inwhich Z is oxygen can be prepared as follows:

2A. In the above reaction scheme, R^(x) is a C₁-C₁₀-alkyl radical and{circumflex over (P)} in the formula IIc is a phosphoranyl radical suchas, for example, triphenylphosphoranyl.

The acetalization of the α,β-diketone IIa to IIb is usually carried outat from −20° C. to 120° C., preferably 0° C. to 85° C., in an inertorganic solvent in the presence of an acid [cf. Khim.-Farm. Zh. (1986),p. 606; J. Chem. Res. Miniprint (1982), p. 2528].

Suitable for use as solvents are aliphatic hydrocarbons such as pentane,hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such astoluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxan, anisole andtetrahydrofuran, alcohols such as methanol, ethanol, n-propanol,isopropanol, n-butanol and tert-butanol, and dimethyl sulfoxide,dimethylformamide and dimethylacetamide, particularly preferablytoluene, methanol, ethanol and dimethylacetamide. It is also possible touse mixtures of the solvents mentioned.

Suitable acids and acid catalysts are inorganic acids such ashydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acidand perchloric acid, Lewis acids such as boron trifluoride, aluminumtrichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chlorideand zinc(II) chloride, and organic acids such as formic acid, aceticacid, propionic acid, oxalic acid, citric acid and trifluoroacetic acid.

In general, the acids are employed in catalytic amounts, but it is alsopossible to employ them in equimolar amounts, in excess or, ifappropriate, as solvent.

In general, the reactants are reacted with one another in equimolaramounts. To improve the yield, it may be advantageous to employ anexcess of C(OR^(x))₃, based on IIa.

The diketones IIa are commercially available or known from theliterature [J. Am. Chem. Soc. (1996), p. 12588; J. Chem. Soc. Chem.Commun. (1987), p. 692; Khim.-Farm. Zh. (1986), p. 606], or they can beprepared according to the literature cited.

2B. In a Wittig reaction, the compound IIb is converted into theα,β-unsaturated acetal IV′ using a phosphorane of the formula IIc.

The Wittig reaction is usually carried out at from −78° C. to 85° C.,preferably −10° C. to 65° C., in an inert organic solvent in thepresence of a base [cf. EP-A 513 580].

Suitable for use as solvents are aromatic hydrocarbons such as toluene,o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether,tert-butyl methyl ether, dioxan, anisole and tetrahydrofuran, anddimethyl sulfoxide, dimethylformamide and dimethylacetamide,particularly preferably tetrahydrofuran, tert-butyl methyl ether,dimethylformamide and dimethylacetamide. It is also possible to employmixtures of the solvents mentioned.

In general, suitable bases are inorganic compounds such as alkali metaland alkaline earth metal hydrides such as lithium hydride, sodiumhydride, potassium hydride and calcium hydride, alkali metal amides suchas lithium amide, sodium amide and potassium amide, organometalliccompounds, in particular alkali metal alkyls such as methyllithium,butyllithium and phenyllithium, alkylmagnesium halides such asmethylmagnesium chloride, and alkali metal and alkaline earth metalalkoxides such as sodium methoxide, sodium ethoxide, potassiummethoxide, potassium tert-butoxide and dimethoxymagnesium. Particularpreference is given to potassium tert-butoxide, sodium tert-butoxide,sodium methoxide, potassium methoxide and sodium hydroxide.

In general, the bases are used in catalytic amounts, but it is alsopossible to employ them in equimolar amounts, in excess or, ifappropriate, as solvent.

In general, the reactants are reacted with one another in equimolaramounts. To improve the yield, it may be advantageous to employ anexcess of IIc, based on IIb.

The phosphoranes of the formula IIc are commercially available or knownfrom the literature [cf. Lieges Ann. Chem. (1967), p. 708; J. Org. Chem.(1983), p. 4860], or they can be prepared according to the literaturecited.

2C. In general, the α,β-unsaturated acetal of the formula IV′ is reactedwith hydroxylamine, or one of its acid addition salts, at from −10° C.to 86° C., preferably 0° C. to 65° C., in an inert organic solvent, ifappropriate in the presence of a base, to give the oxime of the formulaIV [cf. Journal of Organic Chemistry (1993), p. 759; Helv. Chim. Acta(1960), p. 1546].

Suitable for use as solvents are ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxan, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanoland tert-butanol, particularly preferably methanol and ethanol. It isalso possible to employ mixtures of the solvents mentioned.

In general, suitable bases are organic bases, for example tertiaryamines such as trimethylamine, triethylamine, triisopropylethylamine andN-methylpiperidine, pyridine, substituted pyridines such as collidine,lutidine and 4-dimethylaminopyridine, and bicyclic amines. Particularpreference is given to triethylamine and pyridine.

In general, the bases are employed in catalytic amounts, but it is alsopossible to employ them in equimolar amounts, in excess or, ifappropriate, as solvent.

In general, the reactants are reacted with one another in equimolaramounts. To improve the yield, it may be advantageous to employ anexcess of hydroxylamine, based on IV,.

2D. The α,β-unsaturated oxime of the formula IV is converted into theoxirane IIA by oxidation.

In general, the epoxidation is carried out at from −78° C. to 45° C.,preferably −20° C. to 30° C., in an inert organic solvent [cf.Houben-Weyl, Methoden der organischen Chemie, Volume 4/1a, 4th edition,p. 182-239, Georg Thieme Verlag, Stuttgart 1981].

Suitable for use as oxidizing agents are oxygen donors such as inorganicperoxides, for example hydrogen peroxide and tert-butyl hydroperoxide,or organic peracids, for example perbenzoic acid, 3-chloroperbenzoicacid or peracetic acid. In general, they are reacted with one another inequimolar amounts. To improve the yield, it may be advantageous toemploy a 3- to 5-fold excess of the oxidizing agent, based on thecompound IV.

Suitable for use as solvents are aliphatic hydrocarbons such as pentane,hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such astoluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, and dimethyl sulfoxide,dimethylformamide and dimethylacetamide, particularly preferablytoluene, methylene chloride and chlorobenzene. It is also possible touse mixtures of the solvents mentioned.

The starting materials IIB required for preparing the compounds I whereZ is C(R^(a))₂ can be prepared by routes known from the literature asfollows:

3. To prepare the ketone of the formula IIf, the cyclopropylcarboxylicacid derivative of the formula IIf′ [for the preparation see, forexample, EP-A 459 285; Anal. Chem. 24 (1952), p. 623, Journal of organicChemistry 31, (1966), p. 1379] can be reacted with organometallicreagents Mt-R¹, in particular Grignard or lithium reagents [cf. Bull.Chem. Soc. Jap. 68 (1995), p. 341; J. Am. Chem. Soc. 76 (1954), p. 2244;Chem. Ber. 114 (1981), p. 3831; Helv. Chim. Acta 42 (1959), p. 2394].

Furthermore, compounds of the formula I in which Z is oxygen areobtained by reacting a benzyl compound of the formula III with an oximeof the formula IV to give an oxime ether of the formula V which issubsequently converted into a compound of the formula I by oxidation.

4. The preparation of the oxime ether V is carried out in a conventionalmanner, generally at from −20° C. to 85° C., preferably 0° C. to 65° C.,in an inert organic solvent in the presence of a base [cf. EP-A 463488].

4A. A synthetic route to the oxime IV required for preparing thecompounds V has already been described in connection with the synthesisof the compounds IIA.

4B. The oxidation of the unsaturated oxime ether V to the compound ofthe formula I in which Z is oxygen is carried out by a method similar tothe oxidation of the compound IV to the oxirane IIA.

The oxidation is usually carried out at from −78° C. to 45° C.,preferably −20° C. to 30° C., in an inert organic solvent.

Compounds of the formula I in which Z is NH are obtained by reactingcompounds of the formula I in which Z is oxygen with metal azides.

5. This reaction is usually carried out at from −20° C. to 120° C.,preferably −20° C. to 100° C., in an inert organic solvent [cf. Journalof Heterocycl. Chemistry (1991), p. 473 and Tetrahedron (1991), p.5287].

In the reaction scheme above, Mt is an ion from the group of the alkali,alkaline earth or transition metals, or trialkylsilyl, for examplesodium or trimethylsilyl; R^(Y) is a C₁-C₁₀-alkoxy radical, inparticular an ethoxy radical or aryl, for example a phenyl radical.

Suitable for use as solvents are aliphatic hydrocarbons such as pentane,hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such astoluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxan, anisole andtetrahydrofuran, ketones such as acetone, methyl ethyl ketone, diethylketone and tert-butyl methyl ketone, and dimethyl sulfoxide,dimethylformamide and dimethylacetamide, or water, particularlypreferably acetone, dichloromethane, toluene and a water/acetonemixture. It is also possible to use mixtures of the solvents mentioned.

In general, the reactants are reacted with one another in equimolaramounts. To improve the yield, it may be advantageous to employ anexcess of MtN₃, based on I (Z═O).

Additionally, compounds of the formula I in which Z is NH are obtainedby reacting compounds of the formula V withethyl-1-azido-N-(methylsulfonyl)formamidate and subsequently hydrolyzingthe resulting compound V′.

6A. Suitable reaction conditions for reacting the oxime ether V withethyl-1-azido-N-(methylsulfonyl)formamidate are given in Journal ofOrganic Chemistry (1989), p. 3945.

Suitable for use as solvents are aliphatic hydrocarbons such as pentane,hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such astoluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ketones such as acetone, methylethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethylsulfoxide, dimethylformamide and dimethylacetamide, particularlypreferably cyclohexane, methylene chloride, toluene and acetone. It isalso possible to use mixtures of the solvents mentioned.

In general, the reactants are reacted with one another in equimolaramounts. To improve the yield, it may be advantageous to employ a 3- to10-fold excess of ethyl 1-azido-N-(methylsulfonyl)formamidate, based onV.

6B. Ethyl 1-azido-N-(methylsulfonyl)formamidate, required for preparingthe compound V′, is known from the literature [Journal of OrganicChemistry (1989), p. 3945] and can be prepared according to theliterature cited.

The hydrolysis of the compound V′ to give the aziridine of the formula Iin which Z is NH is usually carried out at from 0° C. to 85° C.,preferably 25° C. to 65° C., in an inert organic solvent in the presenceof a base [cf. Journal of Organic Chemistry (1989), p. 3945].

Suitable for use as solvents are ethers such as dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone and diethyl ketone,alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanoland tert-butanol, and water, particularly preferably methanol, ethanoland water. It is also possible to use mixtures of the solventsmentioned.

In general, suitable bases are inorganic compounds such as alkali metalhydroxides and alkaline earth metal hydroxides such as lithiumhydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide,alkali metal carbonates and alkaline earth metal carbonates such aslithium carbonate, potassium carbonate and calcium carbonate, and alkalimetal bicarbonates such as sodium bicarbonate. Particular preference isgiven to sodium hydroxide and potassium hydroxide.

In general, the bases are employed in catalytic amounts, but it is alsopossible to employ them in equimolar amounts, in excess, or, ifappropriate, as solvent.

Compounds of the formula I in which Z is N—C₁-C₄-alkyl are obtained byreacting compounds of the formula I in which Z is NH with alkylatingagents.

7. The alkylation is usually carried out at from −30° C. to 120° C.,preferably −10° C. to 100° C., in an inert organic solvent [cf. Synth.Commun. (1991), p. 239]

Suitable alkylating agents are, for example, alkyl halides such asmethyl iodide and bromoethane, or dialkyl sulfates, for example dimethylsulfate.

Suitable for use as solvents are ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxan, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, alcohols such as methanol, ethanol,n-propanol, isopropanol, n-butanol and tert-butanol, and dimethylsulfoxide, dimethylformamide and dimethylacetamide, particularlypreferably tetrahydrofuran, acetonitrile, acetone and dimethylformamide.It is also possible to use mixtures of the solvents mentioned.

In general, suitable bases are inorganic compounds such as alkali metalhydroxides and alkaline earth metal hydroxides such as lithiumhydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide,alkali metal hydrides and alkaline earth metal hydrides such as lithiumhydride, sodium hydride, potassium hydride and calcium hydride, alkalimetal carbonates and alkaline earth metal carbonates such as lithiumcarbonate, potassium carbonate and calcium carbonate, and alkali metalbicarbonates such as sodium bicarbonate, alkylmagnesium halides such asmethylmagnesium chloride, and alkali metal alkoxides and alkaline earthmetal alkoxides such as sodium methoxide, sodium ethoxide, potassiumethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermoreorganic bases, for example tertiary amines such as trimethylamine,triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine,substituted pyridines such as collidine, lutidine and4-dimethylaminopyridine, and bicyclic amines. Particular preference isgiven to NaHCO₃, K₂CO₃ and triethylamine.

In general, the bases are employed in catalytic amounts, but it is alsopossible to employ them in equimolar amounts, in excess, or, ifappropriate, as solvent.

In general, the reactants are reacted with one another in equimolaramounts. To improve the yield, it may be advantageous to employ anexcess of alkylating agent, based on I (Z═NH). To improve the yield, itmay also be advantageous to add tetrabutylammonium halides, inparticular tetrabutylammonium fluoride.

Alternatively to the direct oxidation of the oxime ether V described inChapter 4A, compounds of the formula I in which Z is oxygen and X isC(═N—OCH₃)—CONHCH₃ are obtained by first converting compounds of theformula V in which X is C(═N—OCH₃)—COOCH₃ under customary condition [cf.EP-A 398 692; EP-A 477 631] into the carboxamide Va and subsequentlyconverting the carboxamide Va into the compound I by oxidation.

8. The oxidation of Va is carried out under the conditions given for theoxidation of the compound V in Chapter 4A.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, phase separation and, if required, chromatographicpurification of the crude products. Some of the intermediates and endproducts are obtained in the form of colorless or slightly brownish,viscous oils, which are purified or freed from volatile components underreduced pressure and at moderately elevated temperature. If theintermediates and end products are obtained as solids, purification canalso be carried out by recrystallization or digestion.

Owing to their C═C and C═N double bonds, the preparation of thecompounds I may yield E/Z isomer mixtures which can be separated intothe individual compounds in a customary manner, for example bycrystallization or chromatography.

However, if the synthesis yields isomer mixtures, a separation isgenerally not necessarily required since in some cases the individualisomers can be converted into one another during the preparation for useor upon use (for example under the action of light, acids or bases).Similar conversions may also occur after the use, for example in thetreatment of plants in the treated plant or in the harmful fungus oranimal pest to be controled.

In the group corresponding to X, with regard to the C═N and C═C doublebond, preference is given to the E isomers of the compounds I(configuration based on the OCH₃ or CH₃ group in relation to thecarbonyl group) with respect to their activity.

In the definitions of the symbols given in the above formulae,collective terms were used which generally represent the followingsubstituents:

Halogen: fluorine, chlorine, bromine and iodine;

C₁-C₄-Alkyl: saturated straight-chain or branched hydrocarbon radicalshaving 1 to 4 carbon atoms, eg. methyl, ethyl, propyl, 1-methylethyl,butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;

C₁-C₄-Haloalkyl: straight-chain or branched alkyl groups having 1 to 4carbon atoms (as mentioned above), it being possible for some or all ofthe hydrogen atoms in these groups to be replaced by halogen atoms asmentioned above, preferably fluorine, chlorine and bromine, eg.C₁-C₂-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl,trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl and pentafluoroethyl;

C₁-C₄-Alkoxy: straight-chain or branched alkyl groups having 1 to 4carbon atoms (as mentioned above) and attached to the skeleton via anoxygen atom (—O—);

C₁-C₄-Haloalkoxy: straight-chain or branched haloalkyl groups having 1to 4 carbon atoms (as mentioned above) and attached to the skeleton viaan oxygen atom (—O—);

C₃-C₄-Alkenyl: unsaturated, straight-chain or branched hydrocarbonradicals having 3 to 4 carbon atoms and a double bond in any position,eg. 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyland 2-methyl-2-propenyl;

C₃-C₄-Alkynyl: straight-chain or branched hydrocarbon groups having 3 to4 carbon atoms and a triple bond in any position, eg. 1-propynyl,2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and 1-methyl-2-propynyl.

With respect to the substitution of the phenyl ring in the position ofR², customary groups are in particular the following substituents:halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

With regard to the intended use of the compounds of the formula I,particular preference is given to the following definitions of thesubstituents, each being on their own or combined:

Particular preference is given to compounds of the formula I in which Xis N(COOCH₃)—OCH₃.

Equally preferred are compounds I in which X is C(CONHCH₃)═N—OCH₃.

Furthermore, preference is given to compounds I in which X isC(COOCH₃)═CH—OCH₃, C(COOCH₃)═N—OCH₃ or C(COOCH₃)═CH—CH₃.

Additionally, preference is given to compounds I in which Y is hydrogen.

In the case that Y is not hydrogen, preference is given to compounds Iin which Y is halogen, C₁-C₂-alkyl, C₁-C₂-haloalkyl or C₁-C₂-alkoxy, inparticular fluorine, chlorine, methyl, trifluoromethyl or methoxy.

Additionally, in the case that Y is not hydrogen, preference is given tocompounds I in which Y is in position 3 or 6.

Particular preference is given to compounds I in which Z is oxygen.

Equally preferred are compounds I in which Z is NR^(a), in particular NHor. NCH₃.

Additionally, preference is given to compounds I in which Z isC(R^(a))2.

Furthermore, particular preference is given to compounds I in which R¹is halogen, in particular fluorine or chlorine.

Additionally, preference is given to compounds I in which R¹ isC₁-C₄-alkyl, in particular methyl.

Equally preferred are compounds I in which R¹ is C_(l)-C₄-haloalkyl, inparticular trifluoromethyl.

Furthermore, preference is given to compounds I in which R² or R³ ishydrogen.

Additionally, preference is given to compounds I in which R² or R³ isC₁-C₂-alkyl.

Furthermore, preference is given to compounds I in which R² is hydrogenand R³ is C₁-C₄-alkyl.

Particular preference is given to compounds I in which R² is phenylwhich is substituted by customary groups.

In the case that Z is oxygen, preference is given to compounds I inwhich R² is hydrogen and R³ is C₁-C₄-alkyl or phenyl which issubstituted by customary groups.

Equally preferred are compounds I in which R⁴ is phenyl with or withoutsubstitution by 1-3 substituents from the following group: halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy orC(R^(b))═N—OR^(c).

Furthermore, preference is given to compounds I in which R⁴ is phenylwhich may be substituted by customary groups in position 4.

The particularly preferred embodiments of the intermediates correspond,with respect to the variables, to those of the radicals R¹, R², R³ andR⁴ of formula I.

Particular preference is given to compounds of the formula Ia.1 where Yis hydrogen, 6-methyl, 6-chloro or 3- or 6- fluoro, R¹ is methyl, ethyl,chloro, trifluoromethyl or methoxy, R² is hydrogen or methyl, R³ ismethyl, ethyl, n- or isopropyl or n- or tert-butyl and R⁴ is methyl,ethyl, n- or isopropyl, n- or tert-butyl or unsubstituted or halogen-,methyl-, methoxy- or alkoxyiminomethylene-substituted phenyl.

Furthermore, preference is given to compounds of the formula Ia.2 whereY is hydrogen, 6-methyl, 6-chloro or 3- or 6- fluoro, R¹ is methyl,ethyl, chloro, trifluoromethyl or methoxy, R² is hydrogen or methyl, R³is methyl, ethyl, n- or isopropyl or n- or tert-butyl and R⁴ is methyl,ethyl, n- or isopropyl, n- or tert-butyl or unsubstituted or halogen-,methyl-, methoxy- or alkoxyiminomethylene-substituted phenyl.

Likewise, particular preference is given to compounds of the formulaIa.3 where Y is hydrogen, 6-methyl, 6-chloro or 3- or 6-fluoro, R¹ ismethyl, ethyl, chloro, trifluoromethyl or methoxy, R² is hydrogen ormethyl, R³ is methyl, ethyl, n- or isopropyl or n- or tert-butyl and R⁴is methyl, ethyl, n- or isopropyl, n- or tert-butyl or unsubstituted orhalogen-, methyl-, methoxy- or alkoxyiminomethylene-substituted phenyl.

Furthermore particular preference is given to compounds of the formulaIa.4 where Y is hydrogen, 6-methyl, 6-chloro or 3- or 6-fluoro, R¹ ismethyl, ethyl, chloro, trifluoromethyl or methoxy, R² is hydrogen ormethyl, R³ is methyl, ethyl, n- or isopropyl or n- or tert-butyl and R⁴is methyl, ethyl, n- or isopropyl, n- or tert-butyl or unsubstituted orhalogen-, methyl-, methoxy- or alkoxyiminomethylene-substituted phenyl.

Particular preference is also given to compounds of the formula Ia.5where Y is hydrogen, 6-methyl, 6-chloro or 3- or 6- fluoro, R¹ ismethyl, ethyl, chloro, trifluoromethyl or methoxy, R² is hydrogen ormethyl, R³ is methyl, ethyl, n- or isopropyl or n- or tert-butyl and R⁴is methyl, ethyl, n- or isopropyl, n- or tert-butyl or unsubstituted orhalogen-, methyl-, methoxy- or alkoxyiminomethylene-substituted phenyl.

Moreover, particular preference is given to compounds IB where Y, R² andR^(a) are hydrogen, R¹ is methyl and X is N(COOCH₃)—OCH₃,C(COOCH₃)═COCH₃, C(COOCH₃)═NOCH₃ or C(COOCH₃)═C-CH₃, R³ is hydrogen ormethyl, R⁴ is methyl or is phenyl which is unsubstituted or substitutedby para halogen and R^(a′) is hydrogen or methyl.

Likewise, particular preference is given to compounds IC where Y ishydrogen, R¹ is methyl, X is N(COOCH₃)—OCH₃, C(COOCH₃)═COCH₃,C(COOCH₃)═NOCH₃ or C(COOCH₃)═C-CH₃, R² is hydrogen, R³ is hydrogen ormethyl, R⁴ is methyl or is phenyl which is unsubstituted or substitutedby para halogen and R^(a) is hydrogen, methyl or ethyl.

With respect to their use, particular preference is given to thecompounds I compiled in the tables below. Moreover, the groups mentionedfor a substituent in the tables are, by themselves and independently ofthe combination in which they are mentioned, a particularly preferredembodiment of the substituent in question.

Table 1

Compounds of the formula Ia.1 in which the combination of thesubstituents Y, R¹, R², R³ and R⁴ corresponds for each compound to a rowof table A

Table 2

Compounds of the formula Ia.2 in which the combination of thesubstituents Y, R¹, R², R³ and R⁴ corresponds for each compound to a rowof table A

Table 3

Compounds of the formula Ia.3 in which the combination of thesubstituents Y, R¹, R², R³ and R⁴ corresponds for each compound to a rowof table A

Table 4

Compounds of the formula Ia.4 in which the combination of thesubstituents Y, R¹, R², R³ and R⁴ corresponds for each compound to a rowof table A

Table 5

Compounds of the formula Ia.5 in which the combination of thesubstituents Y, R¹, R², R³ and R⁴ corresponds for each compound to a rowof table A

Table 6

Compounds of the formula I.B in which Y, R² and R^(a) are each hydrogen,R¹ is methyl and the combination of the radicals X, R³, R⁴ and R^(a′)corresponds for each compound to a row of Table B

Table 7

Compounds of the formula I.C in which Y is hydrogen, R¹ is methyl andthe combination of the radicals X, R², R³, R⁴ and R^(a) corresponds foreach compound to a row of Table C

TABLE A No. Y R¹ R² R³ R⁴ A.1 H CH₃ H H CH₃ A.2 H CH₃ H H ethyl A.3 HCH₃ H H n-propyl A.4 H CH₃ H H isopropyl A.5 H CH₃ H H tert-butyl A.6 HCH₃ H H n-butyl A.7 H CH₃ H H C₆H₅ A.8 H CH₃ H H 2-F—C₆H₄ A.9 H CH₃ H H2-Cl—C₆H₄ A.10 H CH₃ H H 2-CH₃—C₆H₄ A.11 H CH₃ H H 2-CF₃—C₆H₄ A.12 H CH₃H H 3-F—C₆H₄ A.13 H CH₃ H H 3-Cl—C₆H₄ A.14 H CH₃ H H 3-CH₃—C₆H₄ A.15 HCH₃ H H 3-CF₃—C₆H₄ A.16 H CH₃ H H 3-Br—C₆H₄ A.17 H CH₃ H H 4-F—C₆H₄ A.18H CH₃ H H 4-Cl—C₆H₄ A.19 H CH₃ H H 4-CH₃—C₆H₄ A.20 H CH₃ H H 4-CF₃—C₆H₄A.21 H CH₃ H H 4-OCH₃—C₆H₄ A.22 H CH₃ H H 4-OCF₃—C₆H₄ A.23 H CH₃ H H4-Br—C₆H₄ A.24 H CH₃ H H 4-(CH═NOCH₃)—C₆H₄ A.25 H CH₃ H H4-(CH═NOEt)—C₆H₄ A.26 H CH₃ H H 4-[C(CH₃)═NOCH₃]—C₆H₄ A.27 H CH₃ H H4-[C(CH₃)═NOEt)—C₆H₄ A.28 H CH₃ H H 2,4-F₂—C₆H₃ A.29 H CH₃ H H2,4-Cl₂—C₆H₃ A.30 H CH₃ H H 2,4-(CH₃)₂—C₆H₃ A.31 H CH₃ H H 3,5-F₂—C₆H₃A.32 H CH₃ H H 3,5-Cl₂—C₆H₃ A.33 H CH₃ H H 3,5-(CH₃)₂—C₆H₃ A.34 H CH₃ HH 2-F-4-Cl—C₆H₃ A.35 H CH₃ H H 2-Cl-4-F—C₆H₃ A.36 H CH₃ H H 3,4-F₂—C₆H₃A.37 H CH₃ H H 3,4-Cl₂—C₆H₃ A.38 H CH₃ H H 2,3-F₂—C₆H₃ A.39 H CH₃ H CH₃CH₃ A.40 H CH₃ H CH₃ ethyl A.41 H CH₃ H CH₃ n-propyl A.42 H CH₃ H CH₃isopropyl A.43 H CH₃ H CH₃ tert-butyl A.44 H CH₃ H CH₃ n-butyl A.45 HCH₃ H CH₃ C₆H₅ A.46 H CH₃ H CH₃ 2-F—C₆H₄ A.47 H CH₃ H CH₃ 2-Cl—C₆H₄ A.48H CH₃ H CH₃ 2-CH₃—C₆H₄ A.49 H CH₃ H CH₃ 2-CF₃—C₆H₄ A.50 H CH₃ H CH₃3-F—C₆H₄ A.51 H CH₃ H CH₃ 3-Cl—C₆H₄ A.52 H CH₃ H CH₃ 3-CH₃—C₆H₄ A.53 HCH₃ H CH₃ 3-CF₃—C₆H₄ A.54 H CH₃ H CH₃ 3-Br—C₆H₄ A.55 H CH₃ H CH₃4-F—C₆H₄ A.56 H CH₃ H CH₃ 4-Cl—C₆H₄ A.57 H CH₃ H CH₃ 4-CH₃—C₆H₄ A.58 HCH₃ H CH₃ 4-CF₃—C₆H₄ A.59 H CH₃ H CH₃ 4-OCH₃—C₆H₄ A.60 H CH₃ H CH₃4-OCF₃—C₆H₄ A.61 H CH₃ H CH₃ 4-Br—C₆H₄ A.62 H CH₃ H CH₃4-(CH═NOCH₃)—C₆H₄ A.63 H CH₃ H CH₃ 4-(CH═NOEt)—C₆H₄ A.64 H CH₃ H CH₃4-[C(CH₃)═NOCH₃]—C₆H₄ A.65 H CH₃ H CH₃ 4-[C(CH₃)═NOEt)—C₆H₄ A.66 H CH₃ HCH₃ 2,4-F₂—C₆H₃ A.67 H CH₃ H CH₃ 2,4-Cl₂—C₆H₃ A.68 H CH₃ H CH₃2,4-(CH₃)₂—C₆H₃ A.69 H CH₃ H CH₃ 3,5-F₂—C₆H₃ A.70 H CH₃ H CH₃3,5-Cl₂—C₆H₃ A.71 H CH₃ H CH₃ 3,5-(CH₃)₂—C₆H₃ A.72 H CH₃ H CH₃2-F-4-Cl—C₆H₃ A.73 H CH₃ H CH₃ 2-Cl-4-F—C₆H₃ A.74 H CH₃ H CH₃3,4-F₂—C₆H₃ A.75 H CH₃ H CH₃ 3,4-Cl₂—C₆H₃ A.76 H CH₃ H CH₃ 2,3-F₂—C₆H₃A.77 H CH₃ H ethyl CH₃ A.78 H CH₃ H ethyl ethyl A.79 H CH₃ H ethyln-propyl A.80 H CH₃ H ethyl isopropyl A.81 H CH₃ H ethyl tert-butyl A.82H CH₃ H ethyl n-butyl A.83 H CH₃ H ethyl C₆H₅ A.84 H CH₃ H ethyl2-F—C₆H₄ A.85 H CH₃ H ethyl 2-Cl—C₆H₄ A.86 H CH₃ H ethyl 2-CH₃—C₆H₄ A.87H CH₃ H ethyl 2-CF₃—C₆H₄ A.88 H CH₃ H ethyl 3-F—C₆H₄ A.89 H CH₃ H ethyl3-Cl—C₆H₄ A.90 H CH₃ H ethyl 3-CH₃—C₆H₄ A.91 H CH₃ H ethyl 3-CF₃—C₆H₄A.92 H CH₃ H ethyl 3-Br—C₆H₄ A.93 H CH₃ H ethyl 4-F—C₆H₄ A.94 H CH₃ Hethyl 4-Cl—C₆H₄ A.95 H CH₃ H ethyl 4-CH₃—C₆H₄ A.96 H CH₃ H ethyl4-CF₃—C₆H₄ A.97 H CH₃ H ethyl 4-OCH₃—C₆H₄ A.98 H CH₃ H ethyl 4-OCF₃—C₆H₄A.99 H CH₃ H ethyl 4-Br—C₆H₄ A.100 H CH₃ H ethyl 4-(CH═NOCH₃)—C₆H₄ A.101H CH₃ H ethyl 4-(CH═NOEt)—C₆H₄ A.102 H CH₃ H ethyl 4-[C(CH₃)═NOCH₃]—C₆H₄A.103 H CH₃ H ethyl 4-[C(CH₃)═NOEt)—C₆H₄ A.104 H CH₃ H ethyl 2,4-F₂—C₆H₃A.105 H CH₃ H ethyl 2,4-Cl₂—C₆H₃ A.106 H CH₃ H ethyl 2,4-(CH₃)₂—C₆H₃A.107 H CH₃ H ethyl 3,5-F₂—C₆H₃ A.108 H CH₃ H ethyl 3,5-Cl₂—C₆H₃ A.109 HCH₃ H ethyl 3,5-(CH₃)₂—C₆H₃ A.110 H CH₃ H ethyl 2-F-4-Cl—C₆H₃ A.111 HCH₃ H ethyl 2-Cl-4-F—C₆H₃ A.112 H CH₃ H ethyl 3,4-F₂—C₆H₃ A.113 H CH₃ Hethyl 3,4-Cl₂—C₆H₃ A.114 H CH₃ H ethyl 2,3-F₂—C₆H₃ A.115 H CH₃ Hn-propyl CH₃ A.116 H CH₃ H n-propyl ethyl A.117 H CH₃ H n-propyln-propyl A.118 H CH₃ H n-propyl isopropyl A.119 H CH₃ H n-propyltert-butyl A.120 H CH₃ H n-propyl n-butyl A.121 H CH₃ H n-propyl C₆H₅A.122 H CH₃ H n-propyl 2-F—C₆H₄ A.123 H CH₃ H n-propyl 2-Cl—C₆H₄ A.124 HCH₃ H n-propyl 2-CH₃—C₆H₄ A.125 H CH₃ H n-propyl 2-CF₃—C₆H₄ A.126 H CH₃H n-propyl 3-F—C₆H₄ A.127 H CH₃ H n-propyl 3-Cl—C₆H₄ A.128 H CH₃ Hn-propyl 3-CH₃—C₆H₄ A.129 H CH₃ H n-propyl 3-CF₃—C₆H₄ A.130 H CH₃ Hn-propyl 3-Br—C₆H₄ A.131 H CH₃ H n-propyl 4-F—C₆H₄ A.132 H CH₃ Hn-propyl 4-Cl—C₆H₄ A.133 H CH₃ H n-propyl 4-CH₃—C₆H₄ A.134 H CH₃ Hn-propyl 4-CF₃—C₆H₄ A.135 H CH₃ H n-propyl 4-OCH₃—C₆H₄ A.136 H CH₃ Hn-propyl 4-OCF₃—C₆H₄ A.137 H CH₃ H n-propyl 4-Br—C₆H₄ A.138 H CH₃ Hn-propyl 4-(CH═NOCH₃)—C₆H₄ A.139 H CH₃ H n-propyl 4-(CH═NOEt)—C₆H₄ A.140H CH₃ H n-propyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.141 H CH₃ H n-propyl4-[C(CH₃)═NOEt)—C₆H₄ A.142 H CH₃ H n-propyl 2,4-F₂—C₆H₃ A.143 H CH₃ Hn-propyl 2,4-Cl₂—C₆H₃ A.144 H CH₃ H n-propyl 2,4-(CH₃)₂—C₆H₃ A.145 H CH₃H n-propyl 3,5-F₂—C₆H₃ A.146 H CH₃ H n-propyl 3,5-Cl₂—C₆H₃ A.147 H CH₃ Hn-propyl 3,5-(CH₃)₂—C₆H₃ A.148 H CH₃ H n-propyl 2-F-4-Cl—C₆H₃ A.149 HCH₃ H n-propyl 2-Cl-4-F—C₆H₃ A.150 H CH₃ H n-propyl 3,4-F₂—C₆H₃ A.151 HCH₃ H n-propyl 3,4-Cl₂—C₆H₃ A.152 H CH₃ H n-propyl 2,3-F₂—C₆H₃ A.153 HCH₃ H n-propyl CH₃ A.154 H CH₃ H n-propyl ethyl A.155 H CH₃ H n-propyln-propyl A.156 H CH₃ H n-propyl isopropyl A.157 H CH₃ H n-propyltert-butyl A.158 H CH₃ H n-propyl n-butyl A.159 H CH₃ H n-propyl C₆H₅A.160 H CH₃ H n-propyl 2-F—C₆H₄ A.161 H CH₃ H n-propyl 2-Cl—C₆H₄ A.162 HCH₃ H n-propyl 2-CH₃—C₆H₄ A.163 H CH₃ H n-propyl 2-CF₃—C₆H₄ A.164 H CH₃H n-propyl 3-F—C₆H₄ A.165 H CH₃ H n-propyl 3-Cl—C₆H₄ A.166 H CH₃ Hn-propyl 3-CH₃—C₆H₄ A.167 H CH₃ H n-propyl 3-CF₃—C₆H₄ A.168 H CH₃ Hn-propyl 3-Br—C₆H₄ A.169 H CH₃ H n-propyl 4-F—C₆H₄ A.170 H CH₃ Hn-propyl 4-Cl—C₆H₄ A.171 H CH₃ H n-propyl 4-CH₃—C₆H₄ A.172 H CH₃ Hn-propyl 4-CF₃—C₆H₄ A.173 H CH₃ H n-propyl 4-OCH₃—C₆H₄ A.174 H CH₃ Hn-propyl 4-OCF₃—C₆H₄ A.175 H CH₃ H n-propyl 4-Br—C₆H₄ A.176 H CH₃ Hn-propyl 4-(CH═NOCH₃)—C₆H₄ A.177 H CH₃ H n-propyl 4-(CH═NOEt)—C₆H₄ A.178H CH₃ H n-propyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.179 H CH₃ H n-propyl4-[C(CH₃)═NOEt)—C₆H₄ A.180 H CH₃ H n-propyl 2,4-F₂—C₆H₃ A.181 H CH₃ Hn-propyl 2,4-Cl₂—C₆H₃ A.182 H CH₃ H n-propyl 2,4-(CH₃)₂—C₆H₃ A.183 H CH₃H n-propyl 3,5-F₂—C₆H₃ A.184 H CH₃ H n-propyl 3,5-Cl₂—C₆H₃ A.185 H CH₃ Hn-propyl 3,5-(CH₃)₂—C₆H₃ A.186 H CH₃ H n-propyl 2-F-4-Cl—C₆H₃ A.187 HCH₃ H n-propyl 2-Cl-4-F—C₆H₃ A.188 H CH₃ H n-propyl 3,4-F₂—C₆H₃ A.189 HCH₃ H n-propyl 3,4-Cl₂—C₆H₃ A.190 H CH₃ H n-propyl 2,3-F₂—C₆H₃ A.191 HCH₃ H n-butyl CH₃ A.192 H CH₃ H n-butyl ethyl A.193 H CH₃ H n-butyln-propyl A.194 H CH₃ H n-butyl isopropyl A.195 H CH₃ H n-butyltert-butyl A.196 H CH₃ H n-butyl n-butyl A.197 H CH₃ H n-butyl C₆H₅A.198 H CH₃ H n-butyl 2-F—C₆H₄ A.199 H CH₃ H n-butyl 2-Cl—C₆H₄ A.200 HCH₃ H n-butyl 2-CH₃—C₆H₄ A.201 H CH₃ H n-butyl 2-CF₃—C₆H₄ A.202 H CH₃ Hn-butyl 3-F—C₆H₄ A.203 H CH₃ H n-butyl 3-Cl—C₆H₄ A.204 H CH₃ H n-butyl3-CH₃—C₆H₄ A.205 H CH₃ H n-butyl 3-CF₃—C₆H₄ A.206 H CH₃ H n-butyl3-Br—C₆H₄ A.207 H CH₃ H n-butyl 4-F—C₆H₄ A.208 H CH₃ H n-butyl 4-Cl—C₆H₄A.209 H CH₃ H n-butyl 4-CH₃—C₆H₄ A.210 H CH₃ H n-butyl 4-CF₃—C₆H₄ A.211H CH₃ H n-butyl 4-OCH₃—C₆H₄ A.212 H CH₃ H n-butyl 4-OCF₃—C₆H₄ A.213 HCH₃ H n-butyl 4-Br—C₆H₄ A.214 H CH₃ H n-butyl 4-(CH═NOCH₃)—C₆H₄ A.215 HCH₃ H n-butyl 4-(CH═NOEt)—C₆H₄ A.216 H CH₃ H n-butyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.217 H CH₃ H n-butyl 4-[C(CH₃)═NOEt)—C₆H₄ A.218 HCH₃ H n-butyl 2,4-F₂—C₆H₃ A.219 H CH₃ H n-butyl 2,4-Cl₂—C₆H₃ A.220 H CH₃H n-butyl 2,4-(CH₃)₂—C₆H₃ A.221 H CH₃ H n-butyl 3,5-F₂—C₆H₃ A.222 H CH₃H n-butyl 3,5-Cl₂—C₆H₃ A.223 H CH₃ H n-butyl 3,5-(CH₃)₂—C₆H₃ A.224 H CH₃H n-butyl 2-F-4-Cl—C₆H₃ A.225 H CH₃ H n-butyl 2-Cl-4-F—C₆H₃ A.226 H CH₃H n-butyl 3,4-F₂—C₆H₃ A.227 H CH₃ H n-butyl 3,4-Cl₂—C₆H₃ A.228 H CH₃ Hn-butyl 2,3-F₂—C₆H₃ A.229 H CH₃ H n-butyl CH₃ A.230 H CH₃ H n-butylethyl A.231 H CH₃ H n-butyl n-propyl A.232 H CH₃ H n-butyl isopropylA.233 H CH₃ H n-butyl tert-butyl A.234 H CH₃ H n-butyl n-butyl A.235 HCH₃ H n-butyl C₆H₅ A.236 H CH₃ H n-butyl 2-F—C₆H₄ A.237 H CH₃ H n-butyl2-Cl—C₆H₄ A.238 H CH₃ H n-butyl 2-CH₃—C₆H₄ A.239 H CH₃ H n-butyl2-CF₃—C₆H₄ A.240 H CH₃ H n-butyl 3-F—C₆H₄ A.241 H CH₃ H n-butyl3-Cl—C₆H₄ A.242 H CH₃ H n-butyl 3-CH₃—C₆H₄ A.243 H CH₃ H n-butyl3-CF₃—C₆H₄ A.244 H CH₃ H n-butyl 3-Br—C₆H₄ A.245 H CH₃ H n-butyl4-F—C₆H₄ A.246 H CH₃ H n-butyl 4-Cl—C₆H₄ A.247 H CH₃ H n-butyl4-CH₃—C₆H₄ A.248 H CH₃ H n-butyl 4-CF₃—C₆H₄ A.249 H CH₃ H n-butyl4-OCH₃—C₆H₄ A.250 H CH₃ H n-butyl 4-OCF₃—C₆H₄ A.251 H CH₃ H n-butyl4-Br—C₆H₄ A.252 H CH₃ H n-butyl 4-(CH═NOCH₃)—C₆H₄ A.253 H CH₃ H n-butyl4-(CH═NOEt)—C₆H₄ A.254 H CH₃ H n-butyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.255 H CH₃H n-butyl 4-[C(CH₃)═NOEt)—C₆H₄ A.256 H CH₃ H n-butyl 2,4-F₂—C₆H₃ A.257 HCH₃ H n-butyl 2,4-Cl₂—C₆H₃ A.258 H CH₃ H n-butyl 2,4-(CH₃)₂—C₆H₃ A.259 HCH₃ H n-butyl 3,5-F₂—C₆H₃ A.260 H CH₃ H n-butyl 3,5-Cl₂—C₆H₃ A.261 H CH₃H n-butyl 3,5-(CH₃)₂—C₆H₃ A.262 H CH₃ H n-butyl 2-F-4-Cl—C₆H₃ A.263 HCH₃ H n-butyl 2-Cl-4-F—C₆H₃ A.264 H CH₃ H n-butyl 3,4-F₂—C₆H₃ A.265 HCH₃ H n-butyl 3,4-Cl₂—C₆H₃ A.266 H CH₃ H n-butyl 2,3-F₂—C₆H₃ A.267 H CH₃H isopropyl CH₃ A.268 H CH₃ H isopropyl ethyl A.269 H CH₃ H isopropyln-propyl A.270 H CH₃ H isopropyl isopropyl A.271 H CH₃ H isopropyltert-butyl A.272 H CH₃ H isopropyl n-butyl A.273 H CH₃ H isopropyl C₆H₅A.274 H CH₃ H isopropyl 2-F—C₆H₄ A.275 H CH₃ H isopropyl 2-Cl—C₆H₄ A.276H CH₃ H isopropyl 2-CH₃—C₆H₄ A.277 H CH₃ H isopropyl 2-CF₃—C₆H₄ A.278 HCH₃ H isopropyl 3-F—C₆H₄ A.279 H CH₃ H isopropyl 3-Cl—C₆H₄ A.280 H CH₃ Hisopropyl 3-CH₃—C₆H₄ A.281 H CH₃ H isopropyl 3-CF₃—C₆H₄ A.282 H CH₃ Hisopropyl 3-Br—C₆H₄ A.283 H CH₃ H isopropyl 4-F—C₆H₄ A.284 H CH₃ Hisopropyl 4-Cl—C₆H₄ A.285 H CH₃ H isopropyl 4-CH₃—C₆H₄ A.286 H CH₃ Hisopropyl 4-CF₃—C₆H₄ A.287 H CH₃ H isopropyl 4-OCH₃—C₆H₄ A.288 H CH₃ Hisopropyl 4-OCF₃—C₆H₄ A.289 H CH₃ H isopropyl 4-Br—C₆H₄ A.290 H CH₃ Hisopropyl 4-(CH═NOCH₃)—C₆H₄ A.291 H CH₃ H isopropyl 4-(CH═NOEt)—C₆H₄A.292 H CH₃ H isopropyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.293 H CH₃ H isopropyl4-[C(CH₃)═NOEt)—C₆H₄ A.294 H CH₃ H isopropyl 2,4-F₂—C₆H₃ A.295 H CH₃ Hisopropyl 2,4-Cl₂—C₆H₃ A.296 H CH₃ H isopropyl 2,4-(CH₃)₂—C₆H₃ A.297 HCH₃ H isopropyl 3,5-F₂—C₆H₃ A.298 H CH₃ H isopropyl 3,5-Cl₂—C₆H₃ A.299 HCH₃ H isopropyl 3,5-(CH₃)₂—C₆H₃ A.300 H CH₃ H isopropyl 2-F-4-Cl—C₆H₃A.301 H CH₃ H isopropyl 2-Cl-4-F—C₆H₃ A.303 H CH₃ H isopropyl3,4-F₂—C₆H₃ A.302 H CH₃ H isopropyl 3,4-Cl₂—C₆H₃ A.304 H CH₃ H isopropyl2,3-F₂—C₆H₃ A.305 H CH₃ H isopropyl CH₃ A.306 H CH₃ H isopropyl ethylA.307 H CH₃ H isopropyl n-propyl A.308 H CH₃ H isopropyl isopropyl A.309H CH₃ H isopropyl tert-butyl A.310 H CH₃ H isopropyl n-butyl A.311 H CH₃H isopropyl C₆H₅ A.312 H CH₃ H isopropyl 2-F—C₆H₄ A.313 H CH₃ Hisopropyl 2-Cl—C₆H₄ A.314 H CH₃ H isopropyl 2-CH₃—C₆H₄ A.315 H CH₃ Hisopropyl 2-CF₃—C₆H₄ A.316 H CH₃ H isopropyl 3-F—C₆H₄ A.317 H CH₃ Hisopropyl 3-Cl—C₆H₄ A.318 H CH₃ H isopropyl 3-CH₃—C₆H₄ A.319 H CH₃ Hisopropyl 3-CF₃—C₆H₄ A.320 H CH₃ H isopropyl 3-Br—C₆H₄ A.321 H CH₃ Hisopropyl 4-F—C₆H₄ A.322 H CH₃ H isopropyl 4-Cl—C₆H₄ A.323 H CH₃ Hisopropyl 4-CH₃—C₆H₄ A.324 H CH₃ H isopropyl 4-CF₃—C₆H₄ A.325 H CH₃ Hisopropyl 4-OCH₃—C₆H₄ A.326 H CH₃ H isopropyl 4-OCF₃—C₆H₄ A.327 H CH₃ Hisopropyl 4-Br—C₆H₄ A.328 H CH₃ H isopropyl 4-(CH═NOCH₃)—C₆H₄ A.329 HCH₃ H isopropyl 4-(CH═NOEt)—C₆H₄ A.330 H CH₃ H isopropyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.231 H CH₃ H isopropyl 4-[C(CH₃)═NOEt)—C₆H₄ A.332H CH₃ H isopropyl 2,4-F₂—C₆H₃ A.333 H CH₃ H isopropyl 2,4-Cl₂—C₆H₃ A.334H CH₃ H isopropyl 2,4-(CH₃)₂—C₆H₃ A.335 H CH₃ H isopropyl 3,5-F₂—C₆H₃A.336 H CH₃ H isopropyl 3,5-Cl₂—C₆H₃ A.337 H CH₃ H isopropyl3,5-(CH₃)₂—C₆H₃ A.338 H CH₃ H isopropyl 2-F-4-Cl—C₆H₃ A.339 H CH₃ Hisopropyl 2-Cl-4-F—C₆H₃ A.340 H CH₃ H isopropyl 3,4-F₂—C₆H₃ A.341 H CH₃H isopropyl 3,4-Cl₂—C₆H₃ A.342 H CH₃ H isopropyl 2,3-F₂—C₆H₃ A.343 H CH₃H tert-butyl CH₃ A.344 H CH₃ H tert-butyl ethyl A.345 H CH₃ H tert-butyln-propyl A.346 H CH₃ H tert-butyl isopropyl A.347 H CH₃ H tert-butyltert-butyl A.348 H CH₃ H tert-butyl n-butyl A.349 H CH₃ H tert-butylC₆H₅ A.350 H CH₃ H tert-butyl 2-F—C₆H₄ A.351 H CH₃ H tert-butyl2-Cl—C₆H₄ A.352 H CH₃ H tert-butyl 2-CH₃—C₆H₄ A.353 H CH₃ H tert-butyl2-CF₃—C₆H₄ A.354 H CH₃ H tert-butyl 3-F—C₆H₄ A.355 H CH₃ H tert-butyl3-Cl—C₆H₄ A.356 H CH₃ H tert-butyl 3-CH₃—C₆H₄ A.357 H CH₃ H tert-butyl3-CF₃—C₆H₄ A.358 H CH₃ H tert-butyl 3-Br—C₆H₄ A.359 H CH₃ H tert-butyl4-F—C₆H₄ A.360 H CH₃ H tert-butyl 4-Cl—C₆H₄ A.361 H CH₃ H tert-butyl4-CH₃—C₆H₄ A.362 H CH₃ H tert-butyl 4-CF₃—C₆H₄ A.363 H CH₃ H tert-butyl4-OCH₃—C₆H₄ A.364 H CH₃ H tert-butyl 4-OCF₃—C₆H₄ A.365 H CH₃ Htert-butyl 4-Br—C₆H₄ A.366 H CH₃ H tert-butyl 4-(CH═NOCH₃)—C₆H₄ A.367 HCH₃ H tert-butyl 4-(CH═NOEt)—C₆H₄ A.368 H CH₃ H tert-butyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.369 H CH₃ H tert-butyl 4-[C(CH₃)═NOEt)—C₆H₄A.370 H CH₃ H tert-butyl 2,4-F₂—C₆H₃ A.371 H CH₃ H tert-butyl2,4-Cl₂—C₆H₃ A.372 H CH₃ H tert-butyl 2,4-(CH₃)₂—C₆H₃ A.373 H CH₃ Htert-butyl 3,5-F₂—C₆H₃ A.374 H CH₃ H tert-butyl 3,5-Cl₂—C₆H₃ A.375 H CH₃H tert-butyl 3,5-(CH₃)₂—C₆H₃ A.376 H CH₃ H tert-butyl 2-F-4-Cl—C₆H₃A.377 H CH₃ H tert-butyl 2-Cl-4-F—C₆H₃ A.378 H CH₃ H tert-butyl3,4-F₂—C₆H₃ A.379 H CH₃ H tert-butyl 3,4-Cl₂—C₆H₃ A.380 H CH₃ Htert-butyl 2,3-F₂—C₆H₃ A.381 H CH₃ H tert-butyl CH₃ A.382 H CH₃ Htert-butyl ethyl A.383 H CH₃ H tert-butyl n-propyl A.384 H CH₃ Htert-butyl isopropyl A.385 H CH₃ H tert-butyl tert-butyl A.386 H CH₃ Htert-butyl n-butyl A.387 H CH₃ H tert-butyl C₆H₅ A.388 H CH₃ Htert-butyl 2-F—C₆H₄ A.389 H CH₃ H tert-butyl 2-Cl—C₆H₄ A.390 H CH₃ Htert-butyl 2-CH₃—C₆H₄ A.391 H CH₃ H tert-butyl 2-CF₃—C₆H₄ A.392 H CH₃ Htert-butyl 3-F—C₆H₄ A.393 H CH₃ H tert-butyl 3-Cl—C₆H₄ A.394 H CH₃ Htert-butyl 3-CH₃—C₆H₄ A.395 H CH₃ H tert-butyl 3-CF₃—C₆H₄ A.396 H CH₃ Htert-butyl 3-Br—C₆H₄ A.397 H CH₃ H tert-butyl 4-F—C₆H₄ A.398 H CH₃ Htert-butyl 4-Cl—C₆H₄ A.399 H CH₃ H tert-butyl 4-CH₃—C₆H₄ A.400 H CH₃ Htert-butyl 4-CF₃—C₆H₄ A.401 H CH₃ H tert-butyl 4-OCH₃—C₆H₄ A.402 H CH₃ Htert-butyl 4-OCF₃—C₆H₄ A.403 H CH₃ H tert-butyl 4-Br—C₆H₄ A.404 H CH₃ Htert-butyl 4-(CH═NOCH₃)—C₆H₄ A.405 H CH₃ H tert-butyl 4-(CH═NOEt)—C₆H₄A.406 H CH₃ H tert-butyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.407 H CH₃ H tert-butyl4-[C(CH₃)═NOEt)—C₆H₄ A.408 H CH₃ H tert-butyl 2,4-F₂—C₆H₃ A.409 H CH₃ Htert-butyl 2,4-Cl₂—C₆H₃ A.410 H CH₃ H tert-butyl 2,4-(CH₃)₂—C₆H₃ A.411 HCH₃ H tert-butyl 3,5-F₂—C₆H₃ A.412 H CH₃ H tert-butyl 3,5-Cl₂—C₆H₃ A.413H CH₃ H tert-butyl 3,5-(CH₃)₂—C₆H₃ A.414 H CH₃ H tert-butyl2-F-4-Cl—C₆H₃ A.415 H CH₃ H tert-butyl 2-Cl-4-F—C₆H₃ A.416 H CH₃ Htert-butyl 3,4-F₂—C₆H₃ A.417 H CH₃ H tert-butyl 3,4-Cl₂—C₆H₃ A.418 H CH₃H tert-butyl 2,3-F₂—C₆H₃ A.419 H Cl CH₃ CH₃ C₆H₅ A.420 H Cl CH₃ CH₃4-F—C₆H₄ A.421 H Cl CH₃ CH₃ 4-Cl—C₆H₄ A.422 H Cl CH₃ CH₃ CH₃ A.423 H CF₃CH₃ CH₃ C₆H₅ A.424 H CF₃ CH₃ CH₃ 4-F—C₆H₄ A.425 H CF₃ CH₃ CH₃ 4-Cl—C₆H₄A.426 H CF₃ CH₃ CH₃ CH₃ A.427 H OCH₃ CH₃ CH₃ C₆H₅ A.428 H OCH₃ CH₃ CH₃4-F—C₆H₄ A.429 H OCH₃ CH₃ CH₃ 4-Cl—C₆H₄ A.430 H OCH₃ CH₃ CH₃ CH₃ A.4316-CH₃ CH₃ H CH₃ CH₃ A.432 6-CH₃ CH₃ H CH₃ C₆H₅ A.433 6-CH₃ CH₃ H CH₃4-F—C₆H₄ A.434 6-CH₃ CH₃ H CH₃ 4-Cl—C₆H₄ A.435 6-CH₃ CH₃ H ethyl CH₃A.436 6-CH₃ CH₃ H ethyl C₆H₅ A.437 6-CH₃ CH₃ H ethyl 4-F—C₆H₄ A.4386-CH₃ CH₃ H ethyl 4-Cl—C₆H₄ A.439 6-CH₃ CH₃ H n-propyl CH₃ A.440 6-CH₃CH₃ H n-propyl C₆H₅ A.441 6-CH₃ CH₃ H n-propyl 4-F—C₆H₄ A.442 6-CH₃ CH₃H n-propyl 4-Cl—C₆H₄ A.443 6-CH₃ CH₃ H n-butyl CH₃ A.444 6-CH₃ CH₃ Hn-butyl C₆H₅ A.445 6-CH₃ CH₃ H n-butyl 4-F—C₆H₄ A.446 6-CH₃ CH₃ Hn-butyl 4-Cl—C₆H₄ A.447 6-CH₃ ethyl H CH₃ CH₃ A.448 6-CH₃ ethyl H CH₃C₆H₅ A.449 6-CH₃ ethyl H CH₃ 4-F—C₆H₄ A.450 6-CH₃ ethyl H CH₃ 4-Cl—C₆H₄A.451 6-CH₃ ethyl H ethyl CH₃ A.452 6-CH₃ ethyl H ethyl C₆H₅ A.453 6-CH₃ethyl H ethyl 4-F—C₆H₄ A.454 6-CH₃ ethyl H ethyl 4-Cl—C₆H₄ A.455 6-CH₃ethyl H n-propyl CH₃ A.456 6-CH₃ ethyl H n-propyl C₆H₅ A.457 6-CH₃ ethylH n-propyl 4-F—C₆H₄ A.458 6-CH₃ ethyl H n-propyl 4-Cl—C₆H₄ A.459 6-CH₃ethyl H n-butyl CH₃ A.460 6-CH₃ ethyl H n-butyl C₆H₅ A.461 6-CH₃ ethyl Hn-butyl 4-F—C₆H₄ A.462 6-CH₃ ethyl H n-butyl 4-Cl—C₆H₄ A.463 6-Cl CH₃ HCH₃ CH₃ A.464 6-Cl CH₃ H CH₃ C₆H₅ A.465 6-Cl CH₃ H CH₃ 4-F—C₆H₄ A.4666-Cl CH₃ H CH₃ 4-Cl—C₆H₄ A.467 6-Cl CH₃ H ethyl CH₃ A.468 6-Cl CH₃ Hethyl C₆H₅ A.469 6-Cl CH₃ H ethyl 4-F—C₆H₄ A.470 6-Cl CH₃ H ethyl4-Cl—C₆H₄ A.471 6-Cl CH₃ H n-propyl CH₃ A.472 6-Cl CH₃ H n-propyl C₆H₅A.473 6-Cl CH₃ H n-propyl 4-F—C₆H₄ A.474 6-Cl CH₃ H n-propyl 4-Cl—C₆H₄A.475 6-Cl CH₃ H n-butyl CH₃ A.476 6-Cl CH₃ H n-butyl C₆H₅ A.477 6-ClCH₃ H n-butyl 4-F—C₆H₄ A.478 6-Cl CH₃ H n-butyl 4-Cl—C₆H₄ A.479 6-Clethyl H CH₃ CH₃ A.480 6-Cl ethyl H CH₃ C₆H₅ A.481 6-Cl ethyl H CH₃4-F—C₆H₄ A.482 6-Cl ethyl H CH₃ 4-Cl—C₆H₄ A.483 6-Cl ethyl H ethyl CH₃A.484 6-Cl ethyl H ethyl C₆H₅ A.485 6-Cl ethyl H ethyl 4-F—C₆H₄ A.4866-Cl ethyl H ethyl 4-Cl—C₆H₄ A.487 6-Cl ethyl H n-propyl CH₃ A.488 6-Clethyl H n-propyl C₆H₅ A.489 6-Cl ethyl H n-propyl 4-F—C₆H₄ A.490 6-Clethyl H n-propyl 4-Cl—C₆H₄ A.491 6-Cl ethyl H n-butyl CH₃ A.492 6-Clethyl H n-butyl C₆H₅ A.493 6-Cl ethyl H n-butyl 4-F—C₆H₄ A.494 6-Clethyl H n-butyl 4-Cl—C₆H₄ A.495 6-F CH₃ H CH₃ CH₃ A.496 6-F CH₃ H CH₃C₆H₅ A.497 6-F CH₃ H CH₃ 4-F—C₆H₄ A.498 6-F CH₃ H CH₃ 4-Cl—C₆H₄ A.4996-F CH₃ H ethyl CH₃ A.500 6-F CH₃ H ethyl C₆H₅ A.501 6-F CH₃ H ethyl4-F—C₆H₄ A.502 6-F CH₃ H ethyl 4-Cl—C₆H₄ A.503 6-F CH₃ H n-propyl CH₃A.504 6-F CH₃ H n-propyl C₆H₅ A.505 6-F CH₃ H n-propyl 4-F—C₆H₄ A.5066-F CH₃ H n-propyl 4-Cl—C₆H₄ A.507 6-F CH₃ H n-butyl CH₃ A.508 6-F CH₃ Hn-butyl C₆H₅ A.509 6-F CH₃ H n-butyl 4-F—C₆H₄ A.510 6-F CH₃ H n-butyl4-Cl—C₆H₄ A.511 6-F ethyl H CH₃ CH₃ A.512 6-F ethyl H CH₃ C₆H₅ A.513 6-Fethyl H CH₃ 4-F—C₆H₄ A.514 6-F ethyl H CH₃ 4-Cl—C₆H₄ A.515 6-F ethyl Hethyl CH₃ A.516 6-F ethyl H ethyl C₆H₅ A.517 6-F ethyl H ethyl 4-F—C₆H₄A.518 6-F ethyl H ethyl 4-Cl—C₆H₄ A.519 6-F ethyl H n-propyl CH₃ A.5206-F ethyl H n-propyl C₆H₅ A.521 6-F ethyl H n-propyl 4-F—C₆H₄ A.522 6-Fethyl H n-propyl 4-Cl—C₆H₄ A.523 6-F ethyl H n-butyl CH₃ A.524 6-F ethylH n-butyl C₆H₅ A.525 6-F ethyl H n-butyl 4-F—C₆H₄ A.526 6-F ethyl Hn-butyl 4-Cl—C₆H₄ A.527 3-F CH₃ H CH₃ CH₃ A.528 3-F CH₃ H CH₃ C₆H₅ A.5293-F CH₃ H CH₃ 4-F—C₆H₄ A.530 3-F CH₃ H CH₃ 4-Cl—C₆H₄ A.531 3-F CH₃ Hethyl CH₃ A.532 3-F CH₃ H ethyl C₆H₅ A.533 3-F CH₃ H ethyl 4-F—C₆H₄A.534 3-F CH₃ H ethyl 4-Cl—C₆H₄ A.535 3-F CH₃ H n-propyl CH₃ A.536 3-FCH₃ H n-propyl C₆H₅ A.537 3-F CH₃ H n-propyl 4-F—C₆H₄ A.538 3-F CH₃ Hn-propyl 4-Cl—C₆H₄ A.539 3-F CH₃ H n-butyl CH₃ A.540 3-F CH₃ H n-butylC₆H₅ A.541 3-F CH₃ H n-butyl 4-F—C₆H₄ A.542 3-F CH₃ H n-butyl 4-Cl—C₆H₄A.543 3-F ethyl H CH₃ CH₃ A.544 3-F ethyl H CH₃ C₆H₅ A.545 3-F ethyl HCH₃ 4-F—C₆H₄ A.546 3-F ethyl H CH₃ 4-Cl—C₆H₄ A.547 3-F ethyl H ethyl CH₃A.548 3-F ethyl H ethyl C₆H₅ A.549 3-F ethyl H ethyl 4-F—C₆H₄ A.550 3-Fethyl H ethyl 4-Cl—C₆H₄ A.551 3-F ethyl H n-propyl CH₃ A.552 3-F ethyl Hn-propyl C₆H₅ A.553 3-F ethyl H n-propyl 4-F—C₆H₄ A.554 3-F ethyl Hn-propyl 4-Cl—C₆H₄ A.555 3-F ethyl H n-butyl CH₃ A.556 3-F ethyl Hn-butyl C₆H₅ A.557 3-F ethyl H n-butyl 4-F—C₆H₄ A.558 3-F ethyl Hn-butyl 4-Cl—C₆H₄ A.559 H ethyl H H CH₃ A.560 H ethyl H H ethyl A.561 Hethyl H H n-propyl A.562 H ethyl H H isopropyl A.563 H ethyl H Htert-butyl A.564 H ethyl H H n-butyl A.565 H ethyl H H C₆H₅ A.566 Hethyl H H 2-F—C₆H₄ A.567 H ethyl H H 2-Cl—C₆H₄ A.568 H ethyl H H2-CH₃—C₆H₄ A.569 H ethyl H H 2-CF₃—C₆H₄ A.570 H ethyl H H 3-F—C₆H₄ A.571H ethyl H H 3-Cl—C₆H₄ A.572 H ethyl H H 3-CH₃—C₆H₄ A.573 H ethyl H H3-CF₃—C₆H₄ A.574 H ethyl H H 3-Br—C₆H₄ A.575 H ethyl H H 4-F—C₆H₄ A.576H ethyl H H 4-Cl—C₆H₄ A.577 H ethyl H H 4-CH₃—C₆H₄ A.578 H ethyl H H4-CF₃—C₆H₄ A.579 H ethyl H H 4-OCH₃—C₆H₄ A.580 H ethyl H H 4-OCF₃—C₆H₄A.581 H ethyl H H 4-Br—C₆H₄ A.582 H ethyl H H 4-(CH═NOCH₃)—C₆H₄ A.583 Hethyl H H 4-(CH═NOEt)—C₆H₄ A.584 H ethyl H H 4-[C(CH₃)═NOCH₃]—C₆H₄ A.585H ethyl H H 4-[C(CH₃)═NOEt]—C₆H₄ A.586 H ethyl H H 2,4-F₂—C₆H₃ A.587 Hethyl H H 2,4-Cl₂—C₆H₃ A.588 H ethyl H H 2,4-(CH₃)₂—C₆H₃ A.589 H ethyl HH 3,5-F₂—C₆H₃ A.590 H ethyl H H 3,5-Cl₂—C₆H₃ A.591 H ethyl H H3,5-(CH₃)₂—C₆H₃ A.592 H ethyl H H 2-F-4-Cl—C₆H₃ A.593 H ethyl H H2-Cl-4-F—C₆H₃ A.594 H ethyl H H 3,4-F₂—C₆H₃ A.595 H ethyl H H3,4-Cl₂—C₆H₃ A.596 H ethyl H H 2,3-F₂—C₆H₃ A.597 H ethyl H CH₃ CH₃ A.598H ethyl H CH₃ ethyl A.599 H ethyl H CH₃ n-propyl A.600 H ethyl H CH₃isopropyl A.601 H ethyl H CH₃ tert-butyl A.602 H ethyl H CH₃ n-butylA.603 H ethyl H CH₃ C₆H₅ A.604 H ethyl H CH₃ 2-F—C₆H₄ A.605 H ethyl HCH₃ 2-Cl—C₆H₄ A.606 H ethyl H CH₃ 2-CH₃—C₆H₄ A.607 H ethyl H CH₃2-CF₃—C₆H₄ A.608 H ethyl H CH₃ 3-F—C₆H₄ A.609 H ethyl H CH₃ 3-Cl—C₆H₄A.610 H ethyl H CH₃ 3-CH₃—C₆H₄ A.611 H ethyl H CH₃ 3-CF₃—C₆H₄ A.612 Hethyl H CH₃ 3-Br—C₆H₄ A.613 H ethyl H CH₃ 4-F—C₆H₄ A.614 H ethyl H CH₃4-Cl—C₆H₄ A.615 H ethyl H CH₃ 4-CH₃—C₆H₄ A.616 H ethyl H CH₃ 4-CF₃—C₆H₄A.617 H ethyl H CH₃ 4-OCH₃—C₆H₄ A.618 H ethyl H CH₃ 4-OCF₃—C₆H₄ A.619 Hethyl H CH₃ 4-Br—C₆H₄ A.620 H ethyl H CH₃ 4-(CH═NOCH₃)—C₆H₄ A.621 Hethyl H CH₃ 4-(CH═NOEt)—C₆H₄ A.622 H ethyl H CH₃ 4-[C(CH₃)═NOCH₃]—C₆H₄A.623 H ethyl H CH₃ 4-[C(CH₃)═NOEt]—C₆H₄ A.624 H ethyl H CH₃ 2,4-F₂—C₆H₃A.625 H ethyl H CH₃ 2,4-Cl₂—C₆H₃ A.626 H ethyl H CH₃ 2,4-(CH₃)₂—C₆H₃A.627 H ethyl H CH₃ 3,5-F₂—C₆H₃ A.628 H ethyl H CH₃ 3,5-Cl₂—C₆H₃ A.629 Hethyl H CH₃ 3,5-(CH₃)₂—C₆H₃ A.630 H ethyl H CH₃ 2-F-4-Cl—C₆H₃ A.631 Hethyl H CH₃ 2-Cl-4-F—C₆H₃ A.632 H ethyl H CH₃ 3,4-F₂—C₆H₃ A.633 H ethylH CH₃ 3,4-Cl₂—C₆H₃ A.634 H ethyl H CH₃ 2,3-F₂—C₆H₃ A.635 H ethyl H ethylCH₃ A.636 H ethyl H ethyl ethyl A.637 H ethyl H ethyl n-propyl A.638 Hethyl H ethyl isopropyl A.639 H ethyl H ethyl tert-butyl A.640 H ethyl Hethyl n-butyl A.641 H ethyl H ethyl C₆H₅ A.642 H ethyl H ethyl 2-F—C₆H₄A.643 H ethyl H ethyl 2-Cl—C₆H₄ A.644 H ethyl H ethyl 2-CH₃—C₆H₄ A.645 Hethyl H ethyl 2-CF₃—C₆H₄ A.646 H ethyl H ethyl 3-F—C₆H₄ A.647 H ethyl Hethyl 3-Cl—C₆H₄ A.648 H ethyl H ethyl 3-CH₃—C₆H₄ A.649 H ethyl H ethyl3-CF₃—C₆H₄ A.650 H ethyl H ethyl 3-Br—C₆H₄ A.651 H ethyl H ethyl4-F—C₆H₄ A.652 H ethyl H ethyl 4-Cl—C₆H₄ A.653 H ethyl H ethyl4-CH₃—C₆H₄ A.654 H ethyl H ethyl 4-CF₃—C₆H₄ A.655 H ethyl H ethyl4-OCH₃—C₆H₄ A.656 H ethyl H ethyl 4-OCF₃—C₆H₄ A.657 H ethyl H ethyl4-Br—C₆H₄ A.658 H ethyl H ethyl 4-(CH═NOCH₃)—C₆H₄ A.659 H ethyl H ethyl4-(CH═NOEt)—C₆H₄ A.660 H ethyl H ethyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.661 Hethyl H ethyl 4-[C(CH₃)═NOEt]—C₆H₄ A.662 H ethyl H ethyl 2,4-F₂—C₆H₃A.663 H ethyl H ethyl 2,4-Cl₂—C₆H₃ A.664 H ethyl H ethyl 2,4-(CH₃)₂—C₆H₃A.665 H ethyl H ethyl 3,5-F₂—C₆H₃ A.666 H ethyl H ethyl 3,5-Cl₂—C₆H₃A.667 H ethyl H ethyl 3,5-(CH₃)₂—C₆H₃ A.668 H ethyl H ethyl2-F-4-Cl—C₆H₃ A.669 H ethyl H ethyl 2-Cl-4-F—C₆H₃ A.670 H ethyl H ethyl3,4-F₂—C₆H₃ A.671 H ethyl H ethyl 3,4-Cl₂—C₆H₃ A.672 H ethyl H ethyl2,3-F₂—C₆H₃ A.673 H ethyl H n-propyl CH₃ A.674 H ethyl H n-propyl ethylA.675 H ethyl H n-propyl n-propyl A.676 H ethyl H n-propyl isopropylA.677 H ethyl H n-propyl tert-butyl A.678 H ethyl H n-propyl n-butylA.679 H ethyl H n-propyl C₆H₅ A.680 H ethyl H n-propyl 2-F—C₆H₄ A.681 Hethyl H n-propyl 2-Cl—C₆H₄ A.682 H ethyl H n-propyl 2-CH₃—C₆H₄ A.683 Hethyl H n-propyl 2-CF₃—C₆H₄ A.684 H ethyl H n-propyl 3-F—C₆H₄ A.685 Hethyl H n-propyl 3-Cl—C₆H₄ A.686 H ethyl H n-propyl 3-CH₃—C₆H₄ A.687 Hethyl H n-propyl 3-CF₃—C₆H₄ A.688 H ethyl H n-propyl 3-Br—C₆H₄ A.689 Hethyl H n-propyl 4-F—C₆H₄ A.690 H ethyl H n-propyl 4-Cl—C₆H₄ A.691 Hethyl H n-propyl 4-CH₃—C₆H₄ A.692 H ethyl H n-propyl 4-CF₃—C₆H₄ A.693 Hethyl H n-propyl 4-OCH₃—C₆H₄ A.694 H ethyl H n-propyl 4-OCF₃—C₆H₄ A.695H ethyl H n-propyl 4-Br—C₆H₄ A.696 H ethyl H n-propyl 4-(CH═NOCH₃)—C₆H₄A.697 H ethyl H n-propyl 4-(CH═NOEt)—C₆H₄ A.698 H ethyl H n-propyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.699 H ethyl H n-propyl 4-[C(CH₃)═NOEt]—C₆H₄A.700 H ethyl H n-propyl 2,4-F₂—C₆H₃ A.701 H ethyl H n-propyl2,4-Cl₂—C₆H₃ A.702 H ethyl H n-propyl 2,4-(CH₃)₂—C₆H₃ A.703 H ethyl Hn-propyl 3,5-F₂—C₆H₃ A.704 H ethyl H n-propyl 3,5-Cl₂—C₆H₃ A.705 H ethylH n-propyl 3,5-(CH₃)₂—C₆H₃ A.706 H ethyl H n-propyl 2-F-4-Cl—C₆H₃ A.707H ethyl H n-propyl 2-Cl-4-F—C₆H₃ A.708 H ethyl H n-propyl 3,4-F₂—C₆H₃A.709 H ethyl H n-propyl 3,4-Cl₂—C₆H₃ A.710 H ethyl H n-propyl2,3-F₂—C₆H₃ A.711 H ethyl H n-propyl CH₃ A.712 H ethyl H n-propyl ethylA.713 H ethyl H n-propyl n-propyl A.714 H ethyl H n-propyl isopropylA.715 H ethyl H n-propyl tert-butyl A.716 H ethyl H n-propyl n-butylA.717 H ethyl H n-propyl C₆H₅ A.718 H ethyl H n-propyl 2-F—C₆H₄ A.719 Hethyl H n-propyl 2-Cl—C₆H₄ A.720 H ethyl H n-propyl 2-CH₃—C₆H₄ A.721 Hethyl H n-propyl 2-CF₃—C₆H₄ A.722 H ethyl H n-propyl 3-F—C₆H₄ A.723 Hethyl H n-propyl 3-Cl—C₆H₄ A.724 H ethyl H n-propyl 3-CH₃—C₆H₄ A.725 Hethyl H n-propyl 3-CF₃—C₆H₄ A.726 H ethyl H n-propyl 3-Br—C₆H₄ A.727 Hethyl H n-propyl 4-F—C₆H₄ A.728 H ethyl H n-propyl 4-Cl—C₆H₄ A.729 Hethyl H n-propyl 4-CH₃—C₆H₄ A.730 H ethyl H n-propyl 4-CF₃—C₆H₄ A.731 Hethyl H n-propyl 4-OCH₃—C₆H₄ A.732 H ethyl H n-propyl 4-OCF₃—C₆H₄ A.733H ethyl H n-propyl 4-Br—C₆H₄ A.734 H ethyl H n-propyl 4-(CH═NOCH₃)—C₆H₄A.735 H ethyl H n-propyl 4-(CH═NOEt)—C₆H₄ A.736 H ethyl H n-propyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.737 H ethyl H n-propyl 4-[C(CH₃)═NOEt]—C₆H₄A.738 H ethyl H n-propyl 2,4-F₂—C₆H₃ A.739 H ethyl H n-propyl2,4-Cl₂—C₆H₃ A.740 H ethyl H n-propyl 2,4-(CH₃)₂—C₆H₃ A.741 H ethyl Hn-propyl 3,5-F₂—C₆H₃ A.742 H ethyl H n-propyl 3,5-Cl₂—C₆H₃ A.743 H ethylH n-propyl 3,5-(CH₃)₂—C₆H₃ A.744 H ethyl H n-propyl 2-F-4-Cl—C₆H₃ A.745H ethyl H n-propyl 2-Cl-4-F—C₆H₃ A.746 H ethyl H n-propyl 3,4-F₂—C₆H₃A.747 H ethyl H n-propyl 3,4-Cl₂—C₆H₃ A.748 H ethyl H n-propyl2,3-F₂—C₆H₃ A.749 H ethyl H n-butyl CH₃ A.750 H ethyl H n-butyl ethylA.751 H ethyl H n-butyl n-propyl A.752 H ethyl H n-butyl isopropyl A.753H ethyl H n-butyl tert-butyl A.754 H ethyl H n-butyl n-butyl A.755 Hethyl H n-butyl C₆H₅ A.756 H ethyl H n-butyl 2-F—C₆H₄ A.757 H ethyl Hn-butyl 2-Cl—C₆H₄ A.758 H ethyl H n-butyl 2-CH₃—C₆H₄ A.759 H ethyl Hn-butyl 2-CF₃—C₆H₄ A.760 H ethyl H n-butyl 3-F—C₆H₄ A.761 H ethyl Hn-butyl 3-Cl—C₆H₄ A.762 H ethyl H n-butyl 3-CH₃—C₆H₄ A.763 H ethyl Hn-butyl 3-CF₃—C₆H₄ A.764 H ethyl H n-butyl 3-Br—C₆H₄ A.765 H ethyl Hn-butyl 4-F—C₆H₄ A.766 H ethyl H n-butyl 4-Cl—C₆H₄ A.767 H ethyl Hn-butyl 4-CH₃—C₆H₄ A.768 H ethyl H n-butyl 4-CF₃—C₆H₄ A.769 H ethyl Hn-butyl 4-OCH₃—C₆H₄ A.770 H ethyl H n-butyl 4-OCF₃—C₆H₄ A.771 H ethyl Hn-butyl 4-Br—C₆H₄ A.772 H ethyl H n-butyl 4-(CH═NOCH₃)—C₆H₄ A.773 Hethyl H n-butyl 4-(CH═NOEt)—C₆H₄ A.774 H ethyl H n-butyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.775 H ethyl H n-butyl 4-[C(CH₃)═NOEt]—C₆H₄ A.776H ethyl H n-butyl 2,4-F₂—C₆H₃ A.777 H ethyl H n-butyl 2,4-Cl₂—C₆H₃ A.778H ethyl H n-butyl 2,4-(CH₃)₂—C₆H₃ A.779 H ethyl H n-butyl 3,5-F₂—C₆H₃A.780 H ethyl H n-butyl 3,5-Cl₂—C₆H₃ A.781 H ethyl H n-butyl3,5-(CH₃)₂—C₆H₃ A.782 H ethyl H n-butyl 2-F-4-Cl—C₆H₃ A.783 H ethyl Hn-butyl 2-Cl-4-F—C₆H₃ A.784 H ethyl H n-butyl 3,4-F₂—C₆H₃ A.785 H ethylH n-butyl 3,4-Cl₂—C₆H₃ A.786 H ethyl H n-butyl 2,3-F₂—C₆H₃ A.787 H ethylH n-butyl CH₃ A.788 H ethyl H n-butyl ethyl A.789 H ethyl H n-butyln-propyl A.790 H ethyl H n-butyl isopropyl A.791 H ethyl H n-butyltert-butyl A.792 H ethyl H n-butyl n-butyl A.793 H ethyl H n-butyl C₆H₅A.794 H ethyl H n-butyl 2-F—C₆H₄ A.795 H ethyl H n-butyl 2-Cl—C₆H₄ A.796H ethyl H n-butyl 2-CH₃—C₆H₄ A.797 H ethyl H n-butyl 2-CF₃—C₆H₄ A.798 Hethyl H n-butyl 3-F—C₆H₄ A.799 H ethyl H n-butyl 3-Cl—C₆H₄ A.800 H ethylH n-butyl 3-CH₃—C₆H₄ A.801 H ethyl H n-butyl 3-CF₃—C₆H₄ A.802 H ethyl Hn-butyl 3-Br—C₆H₄ A.803 H ethyl H n-butyl 4-F—C₆H₄ A.804 H ethyl Hn-butyl 4-Cl—C₆H₄ A.805 H ethyl H n-butyl 4-CH₃—C₆H₄ A.806 H ethyl Hn-butyl 4-CF₃—C₆H₄ A.807 H ethyl H n-butyl 4-OCH₃—C₆H₄ A.808 H ethyl Hn-butyl 4-OCF₃—C₆H₄ A.809 H ethyl H n-butyl 4-Br—C₆H₄ A.810 H ethyl Hn-butyl 4-(CH═NOCH₃)—C₆H₄ A.811 H ethyl H n-butyl 4-(CH═NOEt)—C₆H₄ A.812H ethyl H n-butyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.813 H ethyl H n-butyl4-[C(CH₃)═NOEt]—C₆H₄ A.814 H ethyl H n-butyl 2,4-F₂—C₆H₃ A.815 H ethyl Hn-butyl 2,4-Cl₂—C₆H₃ A.816 H ethyl H n-butyl 2,4-(CH₃)₂—C₆H₃ A.817 Hethyl H n-butyl 3,5-F₂—C₆H₃ A.818 H ethyl H n-butyl 3,5-Cl₂—C₆H₃ A.819 Hethyl H n-butyl 3,5-(CH₃)₂—C₆H₃ A.820 H ethyl H n-butyl 2-F-4-Cl—C₆H₃A.821 H ethyl H n-butyl 2-Cl-4-F—C₆H₃ A.822 H ethyl H n-butyl3,4-F₂—C₆H₃ A.823 H ethyl H n-butyl 3,4-Cl₂—C₆H₃ A.824 H ethyl H n-butyl2,3-F₂—C₆H₃ A.825 H ethyl H isopropyl CH₃ A.826 H ethyl H isopropylethyl A.827 H ethyl H isopropyl n-propyl A.828 H ethyl H isopropylisopropyl A.829 H ethyl H isopropyl tert-butyl A.830 H ethyl H isopropyln-butyl A.831 H ethyl H isopropyl C₆H₅ A.832 H ethyl H isopropyl2-F—C₆H₄ A.833 H ethyl H isopropyl 2-Cl—C₆H₄ A.834 H ethyl H isopropyl2-CH₃—C₆H₄ A.835 H ethyl H isopropyl 2-CF₃—C₆H₄ A.836 H ethyl Hisopropyl 3-F—C₆H₄ A.837 H ethyl H isopropyl 3-Cl—C₆H₄ A.838 H ethyl Hisopropyl 3-CH₃—C₆H₄ A.839 H ethyl H isopropyl 3-CF₃—C₆H₄ A.840 H ethylH isopropyl 3-Br—C₆H₄ A.841 H ethyl H isopropyl 4-F—C₆H₄ A.842 H ethyl Hisopropyl 4-Cl—C₆H₄ A.843 H ethyl H isopropyl 4-CH₃—C₆H₄ A.844 H ethyl Hisopropyl 4-CF₃—C₆H₄ A.845 H ethyl H isopropyl 4-OCH₃—C₆H₄ A.846 H ethylH isopropyl 4-OCF₃—C₆H₄ A.847 H ethyl H isopropyl 4-Br—C₆H₄ A.848 Hethyl H isopropyl 4-(CH═NOCH₃)—C₆H₄ A.849 H ethyl H isopropyl4-(CH═NOEt)—C₆H₄ A.850 H ethyl H isopropyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.851 Hethyl H isopropyl 4-[C(CH₃)═NOEt]—C₆H₄ A.852 H ethyl H isopropyl2,4-F₂—C₆H₃ A.853 H ethyl H isopropyl 2,4-Cl₂—C₆H₃ A.854 H ethyl Hisopropyl 2,4-(CH₃)₂—C₆H₃ A.855 H ethyl H isopropyl 3,5-F₂—C₆H₃ A.856 Hethyl H isopropyl 3,5-Cl₂—C₆H₃ A.857 H ethyl H isopropyl 3,5-(CH₃)₂—C₆H₃A.858 H ethyl H isopropyl 2-F-4-Cl—C₆H₃ A.859 H ethyl H isopropyl2-Cl-4-F—C₆H₃ A.860 H ethyl H isopropyl 3,4-F₂—C₆H₃ A.861 H ethyl Hisopropyl 3,4-Cl₂—C₆H₃ A.862 H ethyl H isopropyl 2,3-F₂—C₆H₃ A.863 Hethyl H isopropyl CH₃ A.864 H ethyl H isopropyl ethyl A.865 H ethyl Hisopropyl n-propyl A.866 H ethyl H isopropyl isopropyl A.867 H ethyl Hisopropyl tert-butyl A.868 H ethyl H isopropyl n-butyl A.869 H ethyl Hisopropyl C₆H₅ A.870 H ethyl H isopropyl 2-F—C₆H₄ A.871 H ethyl Hisopropyl 2-Cl—C₆H₄ A.872 H ethyl H isopropyl 2-CH₃—C₆H₄ A.873 H ethyl Hisopropyl 2-CF₃—C₆H₄ A.874 H ethyl H isopropyl 3-F—C₆H₄ A.875 H ethyl Hisopropyl 3-Cl—C₆H₄ A.876 H ethyl H isopropyl 3-CH₃—C₆H₄ A.877 H ethyl Hisopropyl 3-CF₃—C₆H₄ A.878 H ethyl H isopropyl 3-Br—C₆H₄ A.879 H ethyl Hisopropyl 4-F—C₆H₄ A.880 H ethyl H isopropyl 4-Cl—C₆H₄ A.881 H ethyl Hisopropyl 4-CH₃—C₆H₄ A.882 H ethyl H isopropyl 4-CF₃—C₆H₄ A.883 H ethylH isopropyl 4-OCH₃—C₆H₄ A.884 H ethyl H isopropyl 4-OCF₃—C₆H₄ A.885 Hethyl H isopropyl 4-Br—C₆H₄ A.886 H ethyl H isopropyl 4-(CH═NOCH₃)—C₆H₄A.887 H ethyl H isopropyl 4-(CH═NOEt)—C₆H₄ A.888 H ethyl H isopropyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.889 H ethyl H isopropyl 4-[C(CH₃)═NOEt]—C₆H₄A.890 H ethyl H isopropyl 2,4-F₂—C₆H₃ A.891 H ethyl H isopropyl2,4-Cl₂—C₆H₃ A.892 H ethyl H isopropyl 2,4-(CH₃)₂—C₆H₃ A.893 H ethyl Hisopropyl 3,5-F₂—C₆H₃ A.894 H ethyl H isopropyl 3,5-Cl₂—C₆H₃ A.895 Hethyl H isopropyl 3,5-(CH₃)₂—C₆H₃ A.896 H ethyl H isopropyl2-F-4-Cl—C₆H₃ A.897 H ethyl H isopropyl 2-Cl-4-F—C₆H₃ A.898 H ethyl Hisopropyl 3,4-F₂—C₆H₃ A.899 H ethyl H isopropyl 3,4-Cl₂—C₆H₃ A.900 Hethyl H isopropyl 2,3-F₂—C₆H₃ A.901 H ethyl H tert-butyl CH₃ A.902 Hethyl H tert-butyl ethyl A.903 H ethyl H tert-butyl n-propyl A.904 Hethyl H tert-butyl isopropyl A.905 H ethyl H tert-butyl tert-butyl A.906H ethyl H tert-butyl n-butyl A.907 H ethyl H tert-butyl C₆H₅ A.908 Hethyl H tert-butyl 2-F—C₆H₄ A.909 H ethyl H tert-butyl 2-Cl—C₆H₄ A.910 Hethyl H tert-butyl 2-CH₃—C₆H₄ A.911 H ethyl H tert-butyl 2-CF₃—C₆H₄A.912 H ethyl H tert-butyl 3-F—C₆H₄ A.913 H ethyl H tert-butyl 3-Cl—C₆H₄A.914 H ethyl H tert-butyl 3-CH₃—C₆H₄ A.915 H ethyl H tert-butyl3-CF₃—C₆H₄ A.916 H ethyl H tert-butyl 3-Br—C₆H₄ A.917 H ethyl Htert-butyl 4-F—C₆H₄ A.918 H ethyl H tert-butyl 4-Cl—C₆H₄ A.919 H ethyl Htert-butyl 4-CH₃—C₆H₄ A.920 H ethyl H tert-butyl 4-CF₃—C₆H₄ A.921 Hethyl H tert-butyl 4-OCH₃—C₆H₄ A.922 H ethyl H tert-butyl 4-OCF₃—C₆H₄A.923 H ethyl H tert-butyl 4-Br—C₆H₄ A.924 H ethyl H tert-butyl4-(CH═NOCH₃)—C₆H₄ A.925 H ethyl H tert-butyl 4-(CH═NOEt)—C₆H₄ A.926 Hethyl H tert-butyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.927 H ethyl H tert-butyl4-[C(CH₃)═NOEt]—C₆H₄ A.928 H ethyl H tert-butyl 2,4-F₂—C₆H₃ A.929 Hethyl H tert-butyl 2,4-Cl₂—C₆H₃ A.930 H ethyl H tert-butyl2,4-(CH₃)₂—C₆H₃ A.931 H ethyl H tert-butyl 3,5-F₂—C₆H₃ A.932 H ethyl Htert-butyl 3,5-Cl₂—C₆H₃ A.933 H ethyl H tert-butyl 3,5-(CH₃)₂—C₆H₃ A.934H ethyl H tert-butyl 2-F-4-Cl—C₆H₃ A.935 H ethyl H tert-butyl2-Cl-4-F—C₆H₃ A.936 H ethyl H tert-butyl 3,4-F₂—C₆H₃ A.937 H ethyl Htert-butyl 3,4-Cl₂—C₆H₃ A.938 H ethyl H tert-butyl 2,3-F₂—C₆H₃ A.939 Hethyl H tert-butyl CH₃ A.940 H ethyl H tert-butyl ethyl A.941 H ethyl Htert-butyl n-propyl A.942 H ethyl H tert-butyl isopropyl A.943 H ethyl Htert-butyl tert-butyl A.944 H ethyl H tert-butyl n-butyl A.945 H ethyl Htert-butyl C₆H₅ A.946 H ethyl H tert-butyl 2-F—C₆H₄ A.947 H ethyl Htert-butyl 2-Cl—C₆H₄ A.948 H ethyl H tert-butyl 2-CH₃—C₆H₄ A.949 H ethylH tert-butyl 2-CF₃—C₆H₄ A.950 H ethyl H tert-butyl 3-F—C₆H₄ A.951 Hethyl H tert-butyl 3-Cl—C₆H₄ A.952 H ethyl H tert-butyl 3-CH₃—C₆H₄ A.953H ethyl H tert-butyl 3-CF₃—C₆H₄ A.954 H ethyl H tert-butyl 3-Br—C₆H₄A.955 H ethyl H tert-butyl 4-F—C₆H₄ A.956 H ethyl H tert-butyl 4-Cl—C₆H₄A.957 H ethyl H tert-butyl 4-CH₃—C₆H₄ A.958 H ethyl H tert-butyl4-CF₃—C₆H₄ A.959 H ethyl H tert-butyl 4-OCH₃—C₆H₄ A.960 H ethyl Htert-butyl 4-OCF₃—C₆H₄ A.961 H ethyl H tert-butyl 4-Br—C₆H₄ A.962 Hethyl H tert-butyl 4-(CH═NOCH₃)—C₆H₄ A.963 H ethyl H tert-butyl4-(CH═NOEt)—C₆H₄ A.964 H ethyl H tert-butyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.965H ethyl H tert-butyl 4-[C(CH₃)═NOEt]—C₆H₄ A.966 H ethyl H tert-butyl2,4-F₂—C₆H₃ A.967 H ethyl H tert-butyl 2,4-Cl₂—C₆H₃ A.968 H ethyl Htert-butyl 2,4-(CH₃)₂—C₆H₃ A.969 H ethyl H tert-butyl 3,5-F₂—C₆H₃ A.970H ethyl H tert-butyl 3,5-Cl₂—C₆H₃ A.971 H ethyl H tert-butyl3,5-(CH₃)₂—C₆H₃ A.972 H ethyl H tert-butyl 2-F-4-Cl—C₆H₃ A.973 H ethyl Htert-butyl 2-Cl-4-F—C₆H₃ A.974 H ethyl H tert-butyl 3,4-F₂—C₆H₃ A.975 Hethyl H tert-butyl 3,4-Cl₂—C₆H₃ A.976 H ethyl H tert-butyl 2,3-F₂—C₆H₃A.977 H Cl H H CH₃ A.978 H Cl H H ethyl A.979 H Cl H H n-propyl A.980 HCl H H isopropyl A.981 H Cl H H tert-butyl A.982 H Cl H H n-butyl A.983H Cl H H C₆H₅ A.984 H Cl H H 2-F—C₆H₄ A.985 H Cl H H 2-Cl—C₆H₄ A.986 HCl H H 2-CH₃—C₆H₄ A.987 H Cl H H 2-CF₃—C₆H₄ A.988 H Cl H H 3-F—C₆H₄A.989 H Cl H H 3-Cl—C₆H₄ A.990 H Cl H H 3-CH₃—C₆H₄ A.991 H Cl H H3-CF₃—C₆H₄ A.992 H Cl H H 3-Br—C₆H₄ A.993 H Cl H H 4-F—C₆H₄ A.994 H Cl HH 4-Cl—C₆H₄ A.995 H Cl H H 4-CH₃—C₆H₄ A.996 H Cl H H 4-CF₃—C₆H₄ A.997 HCl H H 4-OCH₃—C₆H₄ A.998 H Cl H H 4-OCF₃—C₆H₄ A.999 H Cl H H 4-Br—C₆H₄A.1000 H Cl H H 4-(CH═NOCH₃)—C₆H₄ A.1001 H Cl H H 4-(CH═NOEt)—C₆H₄A.1002 H Cl H H 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1003 H Cl H H4-[C(CH₃)═NOEt]—C₆H₄ A.1004 H Cl H H 2,4-F₂—C₆H₃ A.1005 H Cl H H2,4-Cl₂—C₆H₃ A.1006 H Cl H H 2,4-(CH₃)₂—C₆H₃ A.1007 H Cl H H 3,5-F₂—C₆H₃A.1008 H Cl H H 3,5-Cl₂—C₆H₃ A.1009 H Cl H H 3,5-(CH₃)₂—C₆H₃ A.1010 H ClH H 2-F-4-Cl—C₆H₃ A.1011 H Cl H H 2-Cl-4-F—C₆H₃ A.1012 H Cl H H3,4-F₂—C₆H₃ A.1013 H Cl H H 3,4-Cl₂—C₆H₃ A.1014 H Cl H H 2,3-F₂—C₆H₃A.1015 H Cl H CH₃ CH₃ A.1016 H Cl H CH₃ ethyl A.1017 H Cl H CH₃ n-propylA.1018 H Cl H CH₃ isopropyl A.1019 H Cl H CH₃ tert-butyl A.1020 H Cl HCH₃ n-butyl A.1021 H Cl H CH₃ C₆H₅ A.1022 H Cl H CH₃ 2-F—C₆H₄ A.1023 HCl H CH₃ 2-Cl—C₆H₄ A.1024 H Cl H CH₃ 2-CH₃—C₆H₄ A.1025 H Cl H CH₃2-CF₃—C₆H₄ A.1026 H Cl H CH₃ 3-F—C₆H₄ A.1027 H Cl H CH₃ 3-Cl—C₆H₄ A.1028H Cl H CH₃ 3-CH₃—C₆H₄ A.1029 H Cl H CH₃ 3-CF₃—C₆H₄ A.1030 H Cl H CH₃3-Br—C₆H₄ A.1031 H Cl H CH₃ 4-F—C₆H₄ A.1032 H Cl H CH₃ 4-Cl—C₆H₄ A.1033H Cl H CH₃ 4-CH₃—C₆H₄ A.1034 H Cl H CH₃ 4-CF₃—C₆H₄ A.1035 H Cl H CH₃4-OCH₃—C₆H₄ A.1036 H Cl H CH₃ 4-OCF₃—C₆H₄ A.1037 H Cl H CH₃ 4-Br—C₆H₄A.1038 H Cl H CH₃ 4-(CH═NOCH₃)—C₆H₄ A.1039 H Cl H CH₃ 4-(CH═NOEt)—C₆H₄A.1040 H Cl H CH₃ 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1041 H Cl H CH₃4-[C(CH₃)═NOEt]—C₆H₄ A.1042 H Cl H CH₃ 2,4-F₂—C₆H₃ A.1043 H Cl H CH₃2,4-Cl₂—C₆H₃ A.1044 H Cl H CH₃ 2,4-(CH₃)₂—C₆H₃ A.1045 H Cl H CH₃3,5-F₂—C₆H₃ A.1046 H Cl H CH₃ 3,5-Cl₂—C₆H₃ A.1047 H Cl H CH₃3,5-(CH₃)₂—C₆H₃ A.1048 H Cl H CH₃ 2-F-4-Cl—C₆H₃ A.1049 H Cl H CH₃2-Cl-4-F—C₆H₃ A.1050 H Cl H CH₃ 3,4-F₂—C₆H₃ A.1051 H Cl H CH₃3,4-Cl₂—C₆H₃ A.1052 H Cl H CH₃ 2,3-F₂—C₆H₃ A.1053 H Cl H ethyl CH₃A.1054 H Cl H ethyl ethyl A.1055 H Cl H ethyl n-propyl A.1056 H Cl Hethyl isopropyl A.1057 H Cl H ethyl tert-butyl A.1058 H Cl H ethyln-butyl A.1059 H Cl H ethyl C₆H₅ A.1060 H Cl H ethyl 2-F—C₆H₄ A.1061 HCl H ethyl 2-Cl—C₆H₄ A.1062 H Cl H ethyl 2-CH₃—C₆H₄ A.1063 H Cl H ethyl2-CF₃—C₆H₄ A.1064 H Cl H ethyl 3-F—C₆H₄ A.1065 H Cl H ethyl 3-Cl—C₆H₄A.1066 H Cl H ethyl 3-CH₃—C₆H₄ A.1067 H Cl H ethyl 3-CF₃—C₆H₄ A.1068 HCl H ethyl 3-Br—C₆H₄ A.1069 H Cl H ethyl 4-F—C₆H₄ A.1070 H Cl H ethyl4-Cl—C₆H₄ A.1071 H Cl H ethyl 4-CH₃—C₆H₄ A.1072 H Cl H ethyl 4-CF₃—C₆H₄A.1073 H Cl H ethyl 4-OCH₃—C₆H₄ A.1074 H Cl H ethyl 4-OCF₃—C₆H₄ A.1075 HCl H ethyl 4-Br—C₆H₄ A.1076 H Cl H ethyl 4-(CH═NOCH₃)—C₆H₄ A.1077 H Cl Hethyl 4-(CH═NOEt)—C₆H₄ A.1078 H Cl H ethyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1079H Cl H ethyl 4-[C(CH₃)═NOEt]—C₆H₄ A.1080 H Cl H ethyl 2,4-F₂—C₆H₃ A.1081H Cl H ethyl 2,4-Cl₂—C₆H₃ A.1082 H Cl H ethyl 2,4-(CH₃)₂—C₆H₃ A.1083 HCl H ethyl 3,5-F₂—C₆H₃ A.1084 H Cl H ethyl 3,5-Cl₂—C₆H₃ A.1085 H Cl Hethyl 3,5-(CH₃)₂—C₆H₃ A.1086 H Cl H ethyl 2-F-4-Cl—C₆H₃ A.1087 H Cl Hethyl 2-Cl-4-F—C₆H₃ A.1088 H Cl H ethyl 3,4-F₂—C₆H₃ A.1089 H Cl H ethyl3,4-Cl₂—C₆H₃ A.1090 H Cl H ethyl 2,3-F₂—C₆H₃ A.1091 H Cl H n-propyl CH₃A.1092 H Cl H n-propyl ethyl A.1093 H Cl H n-propyl n-propyl A.1094 H ClH n-propyl isopropyl A.1095 H Cl H n-propyl tert-butyl A.1096 H Cl Hn-propyl n-butyl A.1097 H Cl H n-propyl C₆H₅ A.1098 H Cl H n-propyl2-F—C₆H₄ A.1099 H Cl H n-propyl 2-Cl—C₆H₄ A.1100 H Cl H n-propyl2-CH₃—C₆H₄ A.1101 H Cl H n-propyl 2-CF₃—C₆H₄ A.1102 H Cl H n-propyl3-F—C₆H₄ A.1103 H Cl H n-propyl 3-Cl—C₆H₄ A.1104 H Cl H n-propyl3-CH₃—C₆H₄ A.1105 H Cl H n-propyl 3-CF₃—C₆H₄ A.1106 H Cl H n-propyl3-Br—C₆H₄ A.1107 H Cl H n-propyl 4-F—C₆H₄ A.1108 H Cl H n-propyl4-Cl—C₆H₄ A.1109 H Cl H n-propyl 4-CH₃—C₆H₄ A.1110 H Cl H n-propyl4-CF₃—C₆H₄ A.1111 H Cl H n-propyl 4-OCH₃—C₆H₄ A.1112 H Cl H n-propyl4-OCF₃—C₆H₄ A.1113 H Cl H n-propyl 4-Br—C₆H₄ A.1114 H Cl H n-propyl4-(CH═NOCH₃)—C₆H₄ A.1115 H Cl H n-propyl 4-(CH═NOEt)—C₆H₄ A.1116 H Cl Hn-propyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1117 H Cl H n-propyl4-[C(CH₃)═NOEt]—C₆H₄ A.1118 H Cl H n-propyl 2,4-F₂—C₆H₃ A.1119 H Cl Hn-propyl 2,4-Cl₂—C₆H₃ A.1120 H Cl H n-propyl 2,4-(CH₃)₂—C₆H₃ A.1121 H ClH n-propyl 3,5-F₂—C₆H₃ A.1122 H Cl H n-propyl 3,5-Cl₂—C₆H₃ A.1123 H Cl Hn-propyl 3,5-(CH₃)₂—C₆H₃ A.1124 H Cl H n-propyl 2-F-4-Cl—C₆H₃ A.1125 HCl H n-propyl 2-Cl-4-F—C₆H₃ A.1126 H Cl H n-propyl 3,4-F₂—C₆H₃ A.1127 HCl H n-propyl 3,4-Cl₂—C₆H₃ A.1128 H Cl H n-propyl 2,3-F₂—C₆H₃ A.1129 HCl H n-propyl CH₃ A.1130 H Cl H n-propyl ethyl A.1131 H Cl H n-propyln-propyl A.1132 H Cl H n-propyl isopropyl A.1133 H Cl H n-propyltert-butyl A.1134 H Cl H n-propyl n-butyl A.1135 H Cl H n-propyl C₆H₅A.1136 H Cl H n-propyl 2-F—C₆H₄ A.1137 H Cl H n-propyl 2-Cl—C₆H₄ A.1138H Cl H n-propyl 2-CH₃—C₆H₄ A.1139 H Cl H n-propyl 2-CF₃—C₆H₄ A.1140 H ClH n-propyl 3-F—C₆H₄ A.1141 H Cl H n-propyl 3-Cl—C₆H₄ A.1142 H Cl Hn-propyl 3-CH₃—C₆H₄ A.1143 H Cl H n-propyl 3-CF₃—C₆H₄ A.1144 H Cl Hn-propyl 3-Br—C₆H₄ A.1145 H Cl H n-propyl 4-F—C₆H₄ A.1146 H Cl Hn-propyl 4-Cl—C₆H₄ A.1147 H Cl H n-propyl 4-CH₃—C₆H₄ A.1148 H Cl Hn-propyl 4-CF₃—C₆H₄ A.1149 H Cl H n-propyl 4-OCH₃—C₆H₄ A.1150 H Cl Hn-propyl 4-OCF₃—C₆H₄ A.1151 H Cl H n-propyl 4-Br—C₆H₄ A.1152 H Cl Hn-propyl 4-(CH═NOCH₃)—C₆H₄ A.1153 H Cl H n-propyl 4-(CH═NOEt)—C₆H₄A.1154 H Cl H n-propyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1155 H Cl H n-propyl4-[C(CH₃)═NOEt]—C₆H₄ A.1156 H Cl H n-propyl 2,4-F₂—C₆H₃ A.1157 H Cl Hn-propyl 2,4-Cl₂—C₆H₃ A.1158 H Cl H n-propyl 2,4-(CH₃)₂—C₆H₃ A.1159 H ClH n-propyl 3,5-F₂—C₆H₃ A.1160 H Cl H n-propyl 3,5-Cl₂—C₆H₃ A.1161 H Cl Hn-propyl 3,5-(CH₃)₂—C₆H₃ A.1162 H Cl H n-propyl 2-F-4-Cl—C₆H₃ A.1163 HCl H n-propyl 2-Cl-4-F—C₆H₃ A.1164 H Cl H n-propyl 3,4-F₂—C₆H₃ A.1165 HCl H n-propyl 3,4-Cl₂—C₆H₃ A.1166 H Cl H n-propyl 2,3-F₂—C₆H₃ A.1167 HCl H n-butyl CH₃ A.1168 H Cl H n-butyl ethyl A.1169 H Cl H n-butyln-propyl A.1170 H Cl H n-butyl isopropyl A.1171 H Cl H n-butyltert-butyl A.1172 H Cl H n-butyl n-butyl A.1173 H Cl H n-butyl C₆H₅A.1174 H Cl H n-butyl 2-F—C₆H₄ A.1175 H Cl H n-butyl 2-Cl—C₆H₄ A.1176 HCl H n-butyl 2-CH₃—C₆H₄ A.1177 H Cl H n-butyl 2-CF₃—C₆H₄ A.1178 H Cl Hn-butyl 3-F—C₆H₄ A.1179 H Cl H n-butyl 3-Cl—C₆H₄ A.1180 H Cl H n-butyl3-CH₃—C₆H₄ A.1181 H Cl H n-butyl 3-CF₃—C₆H₄ A.1182 H Cl H n-butyl3-Br—C₆H₄ A.1183 H Cl H n-butyl 4-F—C₆H₄ A.1184 H Cl H n-butyl 4-Cl—C₆H₄A.1185 H Cl H n-butyl 4-CH₃—C₆H₄ A.1186 H Cl H n-butyl 4-CF₃—C₆H₄ A.1187H Cl H n-butyl 4-OCH₃—C₆H₄ A.1188 H Cl H n-butyl 4-OCF₃—C₆H₄ A.1189 H ClH n-butyl 4-Br—C₆H₄ A.1190 H Cl H n-butyl 4-(CH═NOCH₃)—C₆H₄ A.1191 H ClH n-butyl 4-(CH═NOEt)—C₆H₄ A.1192 H Cl H n-butyl 4-[C(CH₃)═NOCH₃]—C₆H₄A.1193 H Cl H n-butyl 4-[C(CH₃)═NOEt]—C₆H₄ A.1194 H Cl H n-butyl2,4-F₂—C₆H₃ A.1195 H Cl H n-butyl 2,4-Cl₂—C₆H₃ A.1196 H Cl H n-butyl2,4-(CH₃)₂—C₆H₃ A.1197 H Cl H n-butyl 3,5-F₂—C₆H₃ A.1198 H Cl H n-butyl3,5-Cl₂—C₆H₃ A.1199 H Cl H n-butyl 3,5-(CH₃)₂—C₆H₃ A.1200 H Cl H n-butyl2-F-4-Cl—C₆H₃ A.1201 H Cl H n-butyl 2-Cl-4-F—C₆H₃ A.1202 H Cl H n-butyl3,4-F₂—C₆H₃ A.1203 H Cl H n-butyl 3,4-Cl₂—C₆H₃ A.1204 H Cl H n-butyl2,3-F₂—C₆H₃ A.1205 H Cl H n-butyl CH₃ A.1206 H Cl H n-butyl ethyl A.1207H Cl H n-butyl n-propyl A.1208 H Cl H n-butyl isopropyl A.1209 H Cl Hn-butyl tert-butyl A.1210 H Cl H n-butyl n-butyl A.1211 H Cl H n-butylC₆H₅ A.1212 H Cl H n-butyl 2-F—C₆H₄ A.1213 H Cl H n-butyl 2-Cl—C₆H₄A.1214 H Cl H n-butyl 2-CH₃—C₆H₄ A.1215 H Cl H n-butyl 2-CF₃—C₆H₄ A.1216H Cl H n-butyl 3-F—C₆H₄ A.1217 H Cl H n-butyl 3-Cl—C₆H₄ A.1218 H Cl Hn-butyl 3-CH₃—C₆H₄ A.1219 H Cl H n-butyl 3-CF₃—C₆H₄ A.1220 H Cl Hn-butyl 3-Br—C₆H₄ A.1221 H Cl H n-butyl 4-F—C₆H₄ A.1222 H Cl H n-butyl4-Cl—C₆H₄ A.1223 H Cl H n-butyl 4-CH₃—C₆H₄ A.1224 H Cl H n-butyl4-CF₃—C₆H₄ A.1225 H Cl H n-butyl 4-OCH₃—C₆H₄ A.1226 H Cl H n-butyl4-OCF₃—C₆H₄ A.1227 H Cl H n-butyl 4-Br—C₆H₄ A.1228 H Cl H n-butyl4-(CH═NOCH₃)—C₆H₄ A.1229 H Cl H n-butyl 4-(CH═NOEt)—C₆H₄ A.1230 H Cl Hn-butyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1231 H Cl H n-butyl 4-[C(CH₃)═NOEt]—C₆H₄A.1232 H Cl H n-butyl 2,4-F₂—C₆H₃ A.1233 H Cl H n-butyl 2,4-Cl₂—C₆H₃A.1234 H Cl H n-butyl 2,4-(CH₃)₂—C₆H₃ A.1235 H Cl H n-butyl 3,5-F₂—C₆H₃A.1236 H Cl H n-butyl 3,5-Cl₂—C₆H₃ A.1237 H Cl H n-butyl 3,5-(CH₃)₂—C₆H₃A.1238 H Cl H n-butyl 2-F-4-Cl—C₆H₃ A.1239 H Cl H n-butyl 2-Cl-4-F—C₆H₃A.1240 H Cl H n-butyl 3,4-F₂—C₆H₃ A.1241 H Cl H n-butyl 3,4-Cl₂—C₆H₃A.1242 H Cl H n-butyl 2,3-F₂—C₆H₃ A.1243 H Cl H isopropyl CH₃ A.1244 HCl H isopropyl ethyl A.1245 H Cl H isopropyl n-propyl A.1246 H Cl Hisopropyl isopropyl A.1247 H Cl H isopropyl tert-butyl A.1248 H Cl Hisopropyl n-butyl A.1249 H Cl H isopropyl C₆H₅ A.1250 H Cl H isopropyl2-F—C₆H₄ A.1251 H Cl H isopropyl 2-Cl—C₆H₄ A.1252 H Cl H isopropyl2-CH₃—C₆H₄ A.1253 H Cl H isopropyl 2-CF₃—C₆H₄ A.1254 H Cl H isopropyl3-F—C₆H₄ A.1255 H Cl H isopropyl 3-Cl—C₆H₄ A.1256 H Cl H isopropyl3-CH₃—C₆H₄ A.1257 H Cl H isopropyl 3-CF₃—C₆H₄ A.1258 H Cl H isopropyl3-Br—C₆H₄ A.1259 H Cl H isopropyl 4-F—C₆H₄ A.1260 H Cl H isopropyl4-Cl—C₆H₄ A.1261 H Cl H isopropyl 4-CH₃—C₆H₄ A.1262 H Cl H isopropyl4-CF₃—C₆H₄ A.1263 H Cl H isopropyl 4-OCH₃—C₆H₄ A.1264 H Cl H isopropyl4-OCF₃—C₆H₄ A.1265 H Cl H isopropyl 4-Br—C₆H₄ A.1266 H Cl H isopropyl4-(CH═NOCH₃)—C₆H₄ A.1267 H Cl H isopropyl 4-(CH═NOEt)—C₆H₄ A.1268 H Cl Hisopropyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1269 H Cl H isopropyl4-[C(CH₃)═NOEt]—C₆H₄ A.1270 H Cl H isopropyl 2,4-F₂—C₆H₃ A.1271 H Cl Hisopropyl 2,4-Cl₂—C₆H₃ A.1272 H Cl H isopropyl 2,4-(CH₃)₂—C₆H₃ A.1273 HCl H isopropyl 3,5-F₂—C₆H₃ A.1274 H Cl H isopropyl 3,5-Cl₂—C₆H₃ A.1275 HCl H isopropyl 3,5-(CH₃)₂—C₆H₃ A.1276 H Cl H isopropyl 2-F-4-Cl—C₆H₃A.1277 H Cl H isopropyl 2-Cl-4-F—C₆H₃ A.1278 H Cl H isopropyl3,4-F₂—C₆H₃ A.1279 H Cl H isopropyl 3,4-Cl₂—C₆H₃ A.1280 H Cl H isopropyl2,3-F₂—C₆H₃ A.1281 H Cl H isopropyl CH₃ A.1282 H Cl H isopropyl ethylA.1283 H Cl H isopropyl n-propyl A.1284 H Cl H isopropyl isopropylA.1285 H Cl H isopropyl tert-butyl A.1286 H Cl H isopropyl n-butylA.1287 H Cl H isopropyl C₆H₅ A.1288 H Cl H isopropyl 2-F—C₆H₄ A.1289 HCl H isopropyl 2-Cl—C₆H₄ A.1290 H Cl H isopropyl 2-CH₃—C₆H₄ A.1291 H ClH isopropyl 2-CF₃—C₆H₄ A.1292 H Cl H isopropyl 3-F—C₆H₄ A.1293 H Cl Hisopropyl 3-Cl—C₆H₄ A.1294 H Cl H isopropyl 3-CH₃—C₆H₄ A.1295 H Cl Hisopropyl 3-CF₃—C₆H₄ A.1296 H Cl H isopropyl 3-Br—C₆H₄ A.1297 H Cl Hisopropyl 4-F—C₆H₄ A.1298 H Cl H isopropyl 4-Cl—C₆H₄ A.1299 H Cl Hisopropyl 4-CH₃—C₆H₄ A.1300 H Cl H isopropyl 4-CF₃—C₆H₄ A.1301 H Cl Hisopropyl 4-OCH₃—C₆H₄ A.1303 H Cl H isopropyl 4-OCF₃—C₆H₄ A.1302 H Cl Hisopropyl 4-Br—C₆H₄ A.1304 H Cl H isopropyl 4-(CH═NOCH₃)—C₆H₄ A.1305 HCl H isopropyl 4-(CH═NOEt)—C₆H₄ A.1306 H Cl H isopropyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.1307 H Cl H isopropyl 4-[C(CH₃)═NOEt]—C₆H₄A.1308 H Cl H isopropyl 2,4-F₂—C₆H₃ A.1309 H Cl H isopropyl 2,4-Cl₂—C₆H₃A.1310 H Cl H isopropyl 2,4-(CH₃)₂—C₆H₃ A.1311 H Cl H isopropyl3,5-F₂—C₆H₃ A.1312 H Cl H isopropyl 3,5-Cl₂—C₆H₃ A.1313 H Cl H isopropyl3,5-(CH₃)₂—C₆H₃ A.1314 H Cl H isopropyl 2-F-4-Cl—C₆H₃ A.1315 H Cl Hisopropyl 2-Cl-4-F—C₆H₃ A.1316 H Cl H isopropyl 3,4-F₂—C₆H₃ A.1317 H ClH isopropyl 3,4-Cl₂—C₆H₃ A.1318 H Cl H isopropyl 2,3-F₂—C₆H₃ A.1319 H ClH tert-butyl CH₃ A.1320 H Cl H tert-butyl ethyl A.1321 H Cl H tert-butyln-propyl A.1322 H Cl H tert-butyl isopropyl A.1323 H Cl H tert-butyltert-butyl A.1324 H Cl H tert-butyl n-butyl A.1325 H Cl H tert-butylC₆H₅ A.1326 H Cl H tert-butyl 2-F—C₆H₄ A.1327 H Cl H tert-butyl2-Cl—C₆H₄ A.1328 H Cl H tert-butyl 2-CH₃—C₆H₄ A.1329 H Cl H tert-butyl2-CF₃—C₆H₄ A.1330 H Cl H tert-butyl 3-F—C₆H₄ A.1231 H Cl H tert-butyl3-Cl—C₆H₄ A.1332 H Cl H tert-butyl 3-CH₃—C₆H₄ A.1333 H Cl H tert-butyl3-CF₃—C₆H₄ A.1334 H Cl H tert-butyl 3-Br—C₆H₄ A.1335 H Cl H tert-butyl4-F—C₆H₄ A.1336 H Cl H tert-butyl 4-Cl—C₆H₄ A.1337 H Cl H tert-butyl4-CH₃—C₆H₄ A.1338 H Cl H tert-butyl 4-CF₃—C₆H₄ A.1339 H Cl H tert-butyl4-OCH₃—C₆H₄ A.1340 H Cl H tert-butyl 4-OCF₃—C₆H₄ A.1341 H Cl Htert-butyl 4-Br—C₆H₄ A.1342 H Cl H tert-butyl 4-(CH═NOCH₃)—C₆H₄ A.1343 HCl H tert-butyl 4-(CH═NOEt)—C₆H₄ A.1344 H Cl H tert-butyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.1345 H Cl H tert-butyl 4-[C(CH₃)═NOEt]—C₆H₄A.1346 H Cl H tert-butyl 2,4-F₂—C₆H₃ A.1347 H Cl H tert-butyl2,4-Cl₂—C₆H₃ A.1348 H Cl H tert-butyl 2,4-(CH₃)₂—C₆H₃ A.1349 H Cl Htert-butyl 3,5-F₂—C₆H₃ A.1350 H Cl H tert-butyl 3,5-Cl₂—C₆H₃ A.1351 H ClH tert-butyl 3,5-(CH₃)₂—C₆H₃ A.1352 H Cl H tert-butyl 2-F-4-Cl—C₆H₃A.1353 H Cl H tert-butyl 2-Cl-4-F—C₆H₃ A.1354 H Cl H tert-butyl3,4-F₂—C₆H₃ A.1355 H Cl H tert-butyl 3,4-Cl₂—C₆H₃ A.1356 H Cl Htert-butyl 2,3-F₂—C₆H₃ A.1357 H Cl H tert-butyl CH₃ A.1358 H Cl Htert-butyl ethyl A.1359 H Cl H tert-butyl n-propyl A.1360 H Cl Htert-butyl isopropyl A.1361 H Cl H tert-butyl tert-butyl A.1362 H Cl Htert-butyl n-butyl A.1363 H Cl H tert-butyl C₆H₅ A.1364 H Cl Htert-butyl 2-F—C₆H₄ A.1365 H Cl H tert-butyl 2-Cl—C₆H₄ A.1366 H Cl Htert-butyl 2-CH₃—C₆H₄ A.1367 H Cl H tert-butyl 2-CF₃—C₆H₄ A.1368 H Cl Htert-butyl 3-F—C₆H₄ A.1369 H Cl H tert-butyl 3-Cl—C₆H₄ A.1370 H Cl Htert-butyl 3-CH₃—C₆H₄ A.1371 H Cl H tert-butyl 3-CF₃—C₆H₄ A.1372 H Cl Htert-butyl 3-Br—C₆H₄ A.1373 H Cl H tert-butyl 4-F—C₆H₄ A.1374 H Cl Htert-butyl 4-Cl—C₆H₄ A.1375 H Cl H tert-butyl 4-CH₃—C₆H₄ A.1376 H Cl Htert-butyl 4-CF₃—C₆H₄ A.1377 H Cl H tert-butyl 4-OCH₃—C₆H₄ A.1378 H Cl Htert-butyl 4-OCF₃—C₆H₄ A.1379 H Cl H tert-butyl 4-Br—C₆H₄ A.1380 H Cl Htert-butyl 4-(CH═NOCH₃)—C₆H₄ A.1381 H Cl H tert-butyl 4-(CH═NOEt)—C₆H₄A.1382 H Cl H tert-butyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1383 H Cl H tert-butyl4-[C(CH₃)═NOEt]—C₆H₄ A.1384 H Cl H tert-butyl 2,4-F₂—C₆H₃ A.1385 H Cl Htert-butyl 2,4-Cl₂—C₆H₃ A.1386 H Cl H tert-butyl 2,4-(CH₃)₂—C₆H₃ A.1387H Cl H tert-butyl 3,5-F₂—C₆H₃ A.1388 H Cl H tert-butyl 3,5-Cl₂—C₆H₃A.1389 H Cl H tert-butyl 3,5-(CH₃)₂—C₆H₃ A.1390 H Cl H tert-butyl2-F-4-Cl—C₆H₃ A.1391 H Cl H tert-butyl 2-Cl-4-F—C₆H₃ A.1392 H Cl Htert-butyl 3,4-F₂—C₆H₃ A.1393 H Cl H tert-butyl 3,4-Cl₂—C₆H₃ A.1394 H ClH tert-butyl 2,3-F₂—C₆H₃ A.1395 H OCH₃ H H CH₃ A.1396 H OCH₃ H H ethylA.1397 H OCH₃ H H n-propyl A.1398 H OCH₃ H H isopropyl A.1399 H OCH₃ H Htert-butyl A.1400 H OCH₃ H H n-butyl A.1401 H OCH₃ H H C₆H₅ A.1402 HOCH₃ H H 2-F—C₆H₄ A.1403 H OCH₃ H H 2-Cl—C₆H₄ A.1404 H OCH₃ H H2-CH₃—C₆H₄ A.1405 H OCH₃ H H 2-CF₃—C₆H₄ A.1406 H OCH₃ H H 3-F—C₆H₄A.1407 H OCH₃ H H 3-Cl—C₆H₄ A.1408 H OCH₃ H H 3-CH₃—C₆H₄ A.1409 H OCH₃ HH 3-CF₃—C₆H₄ A.1410 H OCH₃ H H 3-Br—C₆H₄ A.1411 H OCH₃ H H 4-F—C₆H₄A.1412 H OCH₃ H H 4-Cl—C₆H₄ A.1413 H OCH₃ H H 4-CH₃—C₆H₄ A.1414 H OCH₃ HH 4-CF₃—C₆H₄ A.1415 H OCH₃ H H 4-OCH₃—C₆H₄ A.1416 H OCH₃ H H 4-OCF₃—C₆H₄A.1417 H OCH₃ H H 4-Br—C₆H₄ A.1418 H OCH₃ H H 4-(CH═NOCH₃)—C₆H₄ A.1419 HOCH₃ H H 4-(CH═NOEt)—C₆H₄ A.1420 H OCH₃ H H 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1421H OCH₃ H H 4-[C(CH₃)═NOEt]—C₆H₄ A.1422 H OCH₃ H H 2,4-F₂—C₆H₃ A.1423 HOCH₃ H H 2,4-Cl₂—C₆H₃ A.1424 H OCH₃ H H 2,4-(CH₃)₂—C₆H₃ A.1425 H OCH₃ HH 3,5-F₂—C₆H₃ A.1426 H OCH₃ H H 3,5-Cl₂—C₆H₃ A.1427 H OCH₃ H H3,5-(CH₃)₂—C₆H₃ A.1428 H OCH₃ H H 2-F-4-Cl—C₆H₃ A.1429 H OCH₃ H H2-Cl-4-F—C₆H₃ A.1430 H OCH₃ H H 3,4-F₂—C₆H₃ A.1431 H OCH₃ H H3,4-Cl₂—C₆H₃ A.1432 H OCH₃ H H 2,3-F₂—C₆H₃ A.1433 H OCH₃ H CH₃ CH₃A.1434 H OCH₃ H CH₃ ethyl A.1435 H OCH₃ H CH₃ n-propyl A.1436 H OCH₃ HCH₃ isopropyl A.1437 H OCH₃ H CH₃ tert-butyl A.1438 H OCH₃ H CH₃ n-butylA.1439 H OCH₃ H CH₃ C₆H₅ A.1440 H OCH₃ H CH₃ 2-F—C₆H₄ A.1441 H OCH₃ HCH₃ 2-Cl—C₆H₄ A.1442 H OCH₃ H CH₃ 2-CH₃—C₆H₄ A.1443 H OCH₃ H CH₃2-CF₃—C₆H₄ A.1444 H OCH₃ H CH₃ 3-F—C₆H₄ A.1445 H OCH₃ H CH₃ 3-Cl—C₆H₄A.1446 H OCH₃ H CH₃ 3-CH₃—C₆H₄ A.1447 H OCH₃ H CH₃ 3-CF₃—C₆H₄ A.1448 HOCH₃ H CH₃ 3-Br—C₆H₄ A.1449 H OCH₃ H CH₃ 4-F—C₆H₄ A.1450 H OCH₃ H CH₃4-Cl—C₆H₄ A.1451 H OCH₃ H CH₃ 4-CH₃—C₆H₄ A.1452 H OCH₃ H CH₃ 4-CF₃—C₆H₄A.1453 H OCH₃ H CH₃ 4-OCH₃—C₆H₄ A.1454 H OCH₃ H CH₃ 4-OCF₃—C₆H₄ A.1455 HOCH₃ H CH₃ 4-Br—C₆H₄ A.1456 H OCH₃ H CH₃ 4-(CH═NOCH₃)—C₆H₄ A.1457 H OCH₃H CH₃ 4-(CH═NOEt)—C₆H₄ A.1458 H OCH₃ H CH₃ 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1459H OCH₃ H CH₃ 4-[C(CH₃)═NOEt]—C₆H₄ A.1460 H OCH₃ H CH₃ 2,4-F₂—C₆H₃ A.1461H OCH₃ H CH₃ 2,4-Cl₂—C₆H₃ A.1462 H OCH₃ H CH₃ 2,4-(CH₃)₂—C₆H₃ A.1463 HOCH₃ H CH₃ 3,5-F₂—C₆H₃ A.1464 H OCH₃ H CH₃ 3,5-Cl₂—C₆H₃ A.1465 H OCH₃ HCH₃ 3,5-(CH₃)₂—C₆H₃ A.1466 H OCH₃ H CH₃ 2-F-4-Cl—C₆H₃ A.1467 H OCH₃ HCH₃ 2-Cl-4-F—C₆H₃ A.1468 H OCH₃ H CH₃ 3,4-F₂—C₆H₃ A.1469 H OCH₃ H CH₃3,4-Cl₂—C₆H₃ A.1470 H OCH₃ H CH₃ 2,3-F₂—C₆H₃ A.1471 H OCH₃ H ethyl CH₃A.1472 H OCH₃ H ethyl ethyl A.1473 H OCH₃ H ethyl n-propyl A.1474 H OCH₃H ethyl isopropyl A.1475 H OCH₃ H ethyl tert-butyl A.1476 H OCH₃ H ethyln-butyl A.1477 H OCH₃ H ethyl C₆H₅ A.1478 H OCH₃ H ethyl 2-F—C₆H₄ A.1479H OCH₃ H ethyl 2-Cl—C₆H₄ A.1480 H OCH₃ H ethyl 2-CH₃—C₆H₄ A.1481 H OCH₃H ethyl 2-CF₃—C₆H₄ A.1482 H OCH₃ H ethyl 3-F—C₆H₄ A.1483 H OCH₃ H ethyl3-Cl—C₆H₄ A.1484 H OCH₃ H ethyl 3-CH₃—C₆H₄ A.1485 H OCH₃ H ethyl3-CF₃—C₆H₄ A.1486 H OCH₃ H ethyl 3-Br—C₆H₄ A.1487 H OCH₃ H ethyl4-F—C₆H₄ A.1488 H OCH₃ H ethyl 4-Cl—C₆H₄ A.1489 H OCH₃ H ethyl4-CH₃—C₆H₄ A.1490 H OCH₃ H ethyl 4-CF₃—C₆H₄ A.1491 H OCH₃ H ethyl4-OCH₃—C₆H₄ A.1492 H OCH₃ H ethyl 4-OCF₃—C₆H₄ A.1493 H OCH₃ H ethyl4-Br—C₆H₄ A.1494 H OCH₃ H ethyl 4-(CH═NOCH₃)—C₆H₄ A.1495 H OCH₃ H ethyl4-(CH═NOEt)—C₆H₄ A.1496 H OCH₃ H ethyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1497 HOCH₃ H ethyl 4-[C(CH₃)═NOEt]—C₆H₄ A.1498 H OCH₃ H ethyl 2,4-F₂—C₆H₃A.1499 H OCH₃ H ethyl 2,4-Cl₂—C₆H₃ A.1500 H OCH₃ H ethyl 2,4-(CH₃)₂—C₆H₃A.1501 H OCH₃ H ethyl 3,5-F₂—C₆H₃ A.1502 H OCH₃ H ethyl 3,5-Cl₂—C₆H₃A.1503 H OCH₃ H ethyl 3,5-(CH₃)₂—C₆H₃ A.1504 H OCH₃ H ethyl2-F-4-Cl—C₆H₃ A.1505 H OCH₃ H ethyl 2-Cl-4-F—C₆H₃ A.1506 H OCH₃ H ethyl3,4-F₂—C₆H₃ A.1507 H OCH₃ H ethyl 3,4-Cl₂—C₆H₃ A.1508 H OCH₃ H ethyl2,3-F₂—C₆H₃ A.1509 H OCH₃ H n-propyl CH₃ A.1510 H OCH₃ H n-propyl ethylA.1511 H OCH₃ H n-propyl n-propyl A.1512 H OCH₃ H n-propyl isopropylA.1513 H OCH₃ H n-propyl tert-butyl A.1514 H OCH₃ H n-propyl n-butylA.1515 H OCH₃ H n-propyl C₆H₅ A.1516 H OCH₃ H n-propyl 2-F—C₆H₄ A.1517 HOCH₃ H n-propyl 2-Cl—C₆H₄ A.1518 H OCH₃ H n-propyl 2-CH₃—C₆H₄ A.1519 HOCH₃ H n-propyl 2-CF₃—C₆H₄ A.1520 H OCH₃ H n-propyl 3-F—C₆H₄ A.1521 HOCH₃ H n-propyl 3-Cl—C₆H₄ A.1522 H OCH₃ H n-propyl 3-CH₃—C₆H₄ A.1523 HOCH₃ H n-propyl 3-CF₃—C₆H₄ A.1524 H OCH₃ H n-propyl 3-Br—C₆H₄ A.1525 HOCH₃ H n-propyl 4-F—C₆H₄ A.1526 H OCH₃ H n-propyl 4-Cl—C₆H₄ A.1527 HOCH₃ H n-propyl 4-CH₃—C₆H₄ A.1528 H OCH₃ H n-propyl 4-CF₃—C₆H₄ A.1529 HOCH₃ H n-propyl 4-OCH₃—C₆H₄ A.1530 H OCH₃ H n-propyl 4-OCF₃—C₆H₄ A.1531H OCH₃ H n-propyl 4-Br—C₆H₄ A.1532 H OCH₃ H n-propyl 4-(CH═NOCH₃)—C₆H₄A.1533 H OCH₃ H n-propyl 4-(CH═NOEt)—C₆H₄ A.1534 H OCH₃ H n-propyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.1535 H OCH₃ H n-propyl 4-[C(CH₃)═NOEt]—C₆H₄A.1536 H OCH₃ H n-propyl 2,4-F₂—C₆H₃ A.1537 H OCH₃ H n-propyl2,4-Cl₂—C₆H₃ A.1538 H OCH₃ H n-propyl 2,4-(CH₃)₂—C₆H₃ A.1539 H OCH₃ Hn-propyl 3,5-F₂—C₆H₃ A.1540 H OCH₃ H n-propyl 3,5-Cl₂—C₆H₃ A.1541 H OCH₃H n-propyl 3,5-(CH₃)₂—C₆H₃ A.1542 H OCH₃ H n-propyl 2-F-4-Cl—C₆H₃ A.1543H OCH₃ H n-propyl 2-Cl-4-F—C₆H₃ A.1544 H OCH₃ H n-propyl 3,4-F₂—C₆H₃A.1545 H OCH₃ H n-propyl 3,4-Cl₂—C₆H₃ A.1546 H OCH₃ H n-propyl2,3-F₂—C₆H₃ A.1547 H OCH₃ H n-propyl CH₃ A.1548 H OCH₃ H n-propyl ethylA.1549 H OCH₃ H n-propyl n-propyl A.1550 H OCH₃ H n-propyl isopropylA.1551 H OCH₃ H n-propyl tert-butyl A.1552 H OCH₃ H n-propyl n-butylA.1553 H OCH₃ H n-propyl C₆H₅ A.1554 H OCH₃ H n-propyl 2-F—C₆H₄ A.1555 HOCH₃ H n-propyl 2-Cl—C₆H₄ A.1556 H OCH₃ H n-propyl 2-CH₃—C₆H₄ A.1557 HOCH₃ H n-propyl 2-CF₃—C₆H₄ A.1558 H OCH₃ H n-propyl 3-F—C₆H₄ A.1559 HOCH₃ H n-propyl 3-Cl—C₆H₄ A.1560 H OCH₃ H n-propyl 3-CH₃—C₆H₄ A.1561 HOCH₃ H n-propyl 3-CF₃—C₆H₄ A.1562 H OCH₃ H n-propyl 3-Br—C₆H₄ A.1563 HOCH₃ H n-propyl 4-F—C₆H₄ A.1564 H OCH₃ H n-propyl 4-Cl—C₆H₄ A.1565 HOCH₃ H n-propyl 4-CH₃—C₆H₄ A.1566 H OCH₃ H n-propyl 4-CF₃—C₆H₄ A.1567 HOCH₃ H n-propyl 4-OCH₃—C₆H₄ A.1568 H OCH₃ H n-propyl 4-OCF₃—C₆H₄ A.1569H OCH₃ H n-propyl 4-Br—C₆H₄ A.1570 H OCH₃ H n-propyl 4-(CH═NOCH₃)—C₆H₄A.1571 H OCH₃ H n-propyl 4-(CH═NOEt)—C₆H₄ A.1572 H OCH₃ H n-propyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.1573 H OCH₃ H n-propyl 4-[C(CH₃)═NOEt]—C₆H₄A.1574 H OCH₃ H n-propyl 2,4-F₂—C₆H₃ A.1575 H OCH₃ H n-propyl2,4-Cl₂—C₆H₃ A.1576 H OCH₃ H n-propyl 2,4-(CH₃)₂—C₆H₃ A.1577 H OCH₃ Hn-propyl 3,5-F₂—C₆H₃ A.1578 H OCH₃ H n-propyl 3,5-Cl₂—C₆H₃ A.1579 H OCH₃H n-propyl 3,5-(CH₃)₂—C₆H₃ A.1580 H OCH₃ H n-propyl 2-F-4-Cl—C₆H₃ A.1581H OCH₃ H n-propyl 2-Cl-4-F—C₆H₃ A.1582 H OCH₃ H n-propyl 3,4-F₂—C₆H₃A.1583 H OCH₃ H n-propyl 3,4-Cl₂—C₆H₃ A.1584 H OCH₃ H n-propyl2,3-F₂—C₆H₃ A.1585 H OCH₃ H n-butyl CH₃ A.1586 H OCH₃ H n-butyl ethylA.1587 H OCH₃ H n-butyl n-propyl A.1588 H OCH₃ H n-butyl isopropylA.1589 H OCH₃ H n-butyl tert-butyl A.1590 H OCH₃ H n-butyl n-butylA.1591 H OCH₃ H n-butyl C₆H₅ A.1592 H OCH₃ H n-butyl 2-F—C₆H₄ A.1593 HOCH₃ H n-butyl 2-Cl—C₆H₄ A.1594 H OCH₃ H n-butyl 2-CH₃—C₆H₄ A.1595 HOCH₃ H n-butyl 2-CF₃—C₆H₄ A.1596 H OCH₃ H n-butyl 3-F—C₆H₄ A.1597 H OCH₃H n-butyl 3-Cl—C₆H₄ A.1598 H OCH₃ H n-butyl 3-CH₃—C₆H₄ A.1599 H OCH₃ Hn-butyl 3-CF₃—C₆H₄ A.1600 H OCH₃ H n-butyl 3-Br—C₆H₄ A.1601 H OCH₃ Hn-butyl 4-F—C₆H₄ A.1602 H OCH₃ H n-butyl 4-Cl—C₆H₄ A.1603 H OCH₃ Hn-butyl 4-CH₃—C₆H₄ A.1604 H OCH₃ H n-butyl 4-CF₃—C₆H₄ A.1605 H OCH₃ Hn-butyl 4-OCH₃—C₆H₄ A.1606 H OCH₃ H n-butyl 4-OCF₃—C₆H₄ A.1607 H OCH₃ Hn-butyl 4-Br—C₆H₄ A.1608 H OCH₃ H n-butyl 4-(CH═NOCH₃)—C₆H₄ A.1609 HOCH₃ H n-butyl 4-(CH═NOEt)—C₆H₄ A.1610 H OCH₃ H n-butyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.1611 H OCH₃ H n-butyl 4-[C(CH₃)═NOEt]—C₆H₄A.1612 H OCH₃ H n-butyl 2,4-F₂—C₆H₃ A.1613 H OCH₃ H n-butyl 2,4-Cl₂—C₆H₃A.1614 H OCH₃ H n-butyl 2,4-(CH₃)₂—C₆H₃ A.1615 H OCH₃ H n-butyl3,5-F₂—C₆H₃ A.1616 H OCH₃ H n-butyl 3,5-Cl₂—C₆H₃ A.1617 H OCH₃ H n-butyl3,5-(CH₃)₂—C₆H₃ A.1618 H OCH₃ H n-butyl 2-F-4-Cl—C₆H₃ A.1619 H OCH₃ Hn-butyl 2-Cl-4-F—C₆H₃ A.1620 H OCH₃ H n-butyl 3,4-F₂—C₆H₃ A.1621 H OCH₃H n-butyl 3,4-Cl₂—C₆H₃ A.1622 H OCH₃ H n-butyl 2,3-F₂—C₆H₃ A.1623 H OCH₃H n-butyl CH₃ A.1624 H OCH₃ H n-butyl ethyl A.1625 H OCH₃ H n-butyln-propyl A.1626 H OCH₃ H n-butyl isopropyl A.1627 H OCH₃ H n-butyltert-butyl A.1628 H OCH₃ H n-butyl n-butyl A.1629 H OCH₃ H n-butyl C₆H₅A.1630 H OCH₃ H n-butyl 2-F—C₆H₄ A.1631 H OCH₃ H n-butyl 2-Cl—C₆H₄A.1632 H OCH₃ H n-butyl 2-CH₃—C₆H₄ A.1633 H OCH₃ H n-butyl 2-CF₃—C₆H₄A.1634 H OCH₃ H n-butyl 3-F—C₆H₄ A.1635 H OCH₃ H n-butyl 3-Cl—C₆H₄A.1636 H OCH₃ H n-butyl 3-CH₃—C₆H₄ A.1637 H OCH₃ H n-butyl 3-CF₃—C₆H₄A.1638 H OCH₃ H n-butyl 3-Br—C₆H₄ A.1639 H OCH₃ H n-butyl 4-F—C₆H₄A.1640 H OCH₃ H n-butyl 4-Cl—C₆H₄ A.1641 H OCH₃ H n-butyl 4-CH₃—C₆H₄A.1642 H OCH₃ H n-butyl 4-CF₃—C₆H₄ A.1643 H OCH₃ H n-butyl 4-OCH₃—C₆H₄A.1644 H OCH₃ H n-butyl 4-OCF₃—C₆H₄ A.1645 H OCH₃ H n-butyl 4-Br—C₆H₄A.1646 H OCH₃ H n-butyl 4-(CH═NOCH₃)—C₆H₄ A.1647 H OCH₃ H n-butyl4-(CH═NOEt)—C₆H₄ A.1648 H OCH₃ H n-butyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1649 HOCH₃ H n-butyl 4-[C(CH₃)═NOEt]—C₆H₄ A.1650 H OCH₃ H n-butyl 2,4-F₂—C₆H₃A.1651 H OCH₃ H n-butyl 2,4-Cl₂—C₆H₃ A.1652 H OCH₃ H n-butyl2,4-(CH₃)₂—C₆H₃ A.1653 H OCH₃ H n-butyl 3,5-F₂—C₆H₃ A.1654 H OCH₃ Hn-butyl 3,5-Cl₂—C₆H₃ A.1655 H OCH₃ H n-butyl 3,5-(CH₃)₂—C₆H₃ A.1656 HOCH₃ H n-butyl 2-F-4-Cl—C₆H₃ A.1657 H OCH₃ H n-butyl 2-Cl-4-F—C₆H₃A.1658 H OCH₃ H n-butyl 3,4-F₂—C₆H₃ A.1659 H OCH₃ H n-butyl 3,4-Cl₂—C₆H₃A.1660 H OCH₃ H n-butyl 2,3-F₂—C₆H₃ A.1661 H OCH₃ H isopropyl CH₃ A.1662H OCH₃ H isopropyl ethyl A.1663 H OCH₃ H isopropyl n-propyl A.1664 HOCH₃ H isopropyl isopropyl A.1665 H OCH₃ H isopropyl tert-butyl A.1666 HOCH₃ H isopropyl n-butyl A.1667 H OCH₃ H isopropyl C₆H₅ A.1668 H OCH₃ Hisopropyl 2-F—C₆H₄ A.1669 H OCH₃ H isopropyl 2-Cl—C₆H₄ A.1670 H OCH₃ Hisopropyl 2-CH₃—C₆H₄ A.1671 H OCH₃ H isopropyl 2-CF₃—C₆H₄ A.1672 H OCH₃H isopropyl 3-F—C₆H₄ A.1673 H OCH₃ H isopropyl 3-Cl—C₆H₄ A.1674 H OCH₃ Hisopropyl 3-CH₃—C₆H₄ A.1675 H OCH₃ H isopropyl 3-CF₃—C₆H₄ A.1676 H OCH₃H isopropyl 3-Br—C₆H₄ A.1677 H OCH₃ H isopropyl 4-F—C₆H₄ A.1678 H OCH₃ Hisopropyl 4-Cl—C₆H₄ A.1679 H OCH₃ H isopropyl 4-CH₃—C₆H₄ A.1680 H OCH₃ Hisopropyl 4-CF₃—C₆H₄ A.1681 H OCH₃ H isopropyl 4-OCH₃—C₆H₄ A.1682 H OCH₃H isopropyl 4-OCF₃—C₆H₄ A.1683 H OCH₃ H isopropyl 4-Br—C₆H₄ A.1684 HOCH₃ H isopropyl 4-(CH═NOCH₃)—C₆H₄ A.1685 H OCH₃ H isopropyl4-(CH═NOEt)—C₆H₄ A.1686 H OCH₃ H isopropyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1687H OCH₃ H isopropyl 4-[C(CH₃)═NOEt]—C₆H₄ A.1688 H OCH₃ H isopropyl2,4-F₂—C₆H₃ A.1689 H OCH₃ H isopropyl 2,4-Cl₂—C₆H₃ A.1690 H OCH₃ Hisopropyl 2,4-(CH₃)₂—C₆H₃ A.1691 H OCH₃ H isopropyl 3,5-F₂—C₆H₃ A.1692 HOCH₃ H isopropyl 3,5-Cl₂—C₆H₃ A.1693 H OCH₃ H isopropyl 3,5-(CH₃)₂—C₆H₃A.1694 H OCH₃ H isopropyl 2-F-4-Cl—C₆H₃ A.1695 H OCH₃ H isopropyl2-Cl-4-F—C₆H₃ A.1696 H OCH₃ H isopropyl 3,4-F₂—C₆H₃ A.1697 H OCH₃ Hisopropyl 3,4-Cl₂—C₆H₃ A.1698 H OCH₃ H isopropyl 2,3-F₂—C₆H₃ A.1699 HOCH₃ H isopropyl CH₃ A.1700 H OCH₃ H isopropyl ethyl A.1701 H OCH₃ Hisopropyl n-propyl A.1702 H OCH₃ H isopropyl isopropyl A.1703 H OCH₃ Hisopropyl tert-butyl A.1704 H OCH₃ H isopropyl n-butyl A.1705 H OCH₃ Hisopropyl C₆H₅ A.1706 H OCH₃ H isopropyl 2-F—C₆H₄ A.1707 H OCH₃ Hisopropyl 2-Cl—C₆H₄ A.1708 H OCH₃ H isopropyl 2-CH₃—C₆H₄ A.1709 H OCH₃ Hisopropyl 2-CF₃—C₆H₄ A.1710 H OCH₃ H isopropyl 3-F—C₆H₄ A.1711 H OCH₃ Hisopropyl 3-Cl—C₆H₄ A.1712 H OCH₃ H isopropyl 3-CH₃—C₆H₄ A.1713 H OCH₃ Hisopropyl 3-CF₃—C₆H₄ A.1714 H OCH₃ H isopropyl 3-Br—C₆H₄ A.1715 H OCH₃ Hisopropyl 4-F—C₆H₄ A.1716 H OCH₃ H isopropyl 4-Cl—C₆H₄ A.1717 H OCH₃ Hisopropyl 4-CH₃—C₆H₄ A.1718 H OCH₃ H isopropyl 4-CF₃—C₆H₄ A.1719 H OCH₃H isopropyl 4-OCH₃—C₆H₄ A.1720 H OCH₃ H isopropyl 4-OCF₃—C₆H₄ A.1721 HOCH₃ H isopropyl 4-Br—C₆H₄ A.1722 H OCH₃ H isopropyl 4-(CH═NOCH₃)—C₆H₄A.1723 H OCH₃ H isopropyl 4-(CH═NOEt)—C₆H₄ A.1724 H OCH₃ H isopropyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.1725 H OCH₃ H isopropyl 4-[C(CH₃)═NOEt]—C₆H₄A.1726 H OCH₃ H isopropyl 2,4-F₂—C₆H₃ A.1727 H OCH₃ H isopropyl2,4-Cl₂—C₆H₃ A.1728 H OCH₃ H isopropyl 2,4-(CH₃)₂—C₆H₃ A.1729 H OCH₃ Hisopropyl 3,5-F₂—C₆H₃ A.1730 H OCH₃ H isopropyl 3,5-Cl₂—C₆H₃ A.1731 HOCH₃ H isopropyl 3,5-(CH₃)₂—C₆H₃ A.1732 H OCH₃ H isopropyl 2-F-4-Cl—C₆H₃A.1733 H OCH₃ H isopropyl 2-Cl-4-F—C₆H₃ A.1734 H OCH₃ H isopropyl3,4-F₂—C₆H₃ A.1735 H OCH₃ H isopropyl 3,4-Cl₂—C₆H₃ A.1736 H OCH₃ Hisopropyl 2,3-F₂—C₆H₃ A.1737 H OCH₃ H tert-butyl CH₃ A.1738 H OCH₃ Htert-butyl ethyl A.1739 H OCH₃ H tert-butyl n-propyl A.1740 H OCH₃ Htert-butyl isopropyl A.1741 H OCH₃ H tert-butyl tert-butyl A.1742 H OCH₃H tert-butyl n-butyl A.1743 H OCH₃ H tert-butyl C₆H₅ A.1744 H OCH₃ Htert-butyl 2-F—C₆H₄ A.1745 H OCH₃ H tert-butyl 2-Cl—C₆H₄ A.1746 H OCH₃ Htert-butyl 2-CH₃—C₆H₄ A.1747 H OCH₃ H tert-butyl 2-CF₃—C₆H₄ A.1748 HOCH₃ H tert-butyl 3-F—C₆H₄ A.1749 H OCH₃ H tert-butyl 3-Cl—C₆H₄ A.1750 HOCH₃ H tert-butyl 3-CH₃—C₆H₄ A.1751 H OCH₃ H tert-butyl 3-CF₃—C₆H₄A.1752 H OCH₃ H tert-butyl 3-Br—C₆H₄ A.1753 H OCH₃ H tert-butyl 4-F—C₆H₄A.1754 H OCH₃ H tert-butyl 4-Cl—C₆H₄ A.1755 H OCH₃ H tert-butyl4-CH₃—C₆H₄ A.1756 H OCH₃ H tert-butyl 4-CF₃—C₆H₄ A.1757 H OCH₃ Htert-butyl 4-OCH₃—C₆H₄ A.1758 H OCH₃ H tert-butyl 4-OCF₃—C₆H₄ A.1759 HOCH₃ H tert-butyl 4-Br—C₆H₄ A.1760 H OCH₃ H tert-butyl 4-(CH═NOCH₃)—C₆H₄A.1761 H OCH₃ H tert-butyl 4-(CH═NOEt)—C₆H₄ A.1762 H OCH₃ H tert-butyl4-[C(CH₃)═NOCH₃]—C₆H₄ A.1763 H OCH₃ H tert-butyl 4-[C(CH₃)═NOEt]—C₆H₄A.1764 H OCH₃ H tert-butyl 2,4-F₂—C₆H₃ A.1765 H OCH₃ H tert-butyl2,4-Cl₂—C₆H₃ A.1766 H OCH₃ H tert-butyl 2,4-(CH₃)₂—C₆H₃ A.1767 H OCH₃ Htert-butyl 3,5-F₂—C₆H₃ A.1768 H OCH₃ H tert-butyl 3,5-Cl₂—C₆H₃ A.1769 HOCH₃ H tert-butyl 3,5-(CH₃)₂—C₆H₃ A.1770 H OCH₃ H tert-butyl2-F-4-Cl—C₆H₃ A.1771 H OCH₃ H tert-butyl 2-Cl-4-F—C₆H₃ A.1772 H OCH₃ Htert-butyl 3,4-F₂—C₆H₃ A.1773 H OCH₃ H tert-butyl 3,4-Cl₂—C₆H₃ A.1774 HOCH₃ H tert-butyl 2,3-F₂—C₆H₃ A.1775 H OCH₃ H tert-butyl CH₃ A.1776 HOCH₃ H tert-butyl ethyl A.1777 H OCH₃ H tert-butyl n-propyl A.1778 HOCH₃ H tert-butyl isopropyl A.1779 H OCH₃ H tert-butyl tert-butyl A.1780H OCH₃ H tert-butyl n-butyl A.1781 H OCH₃ H tert-butyl C₆H₅ A.1782 HOCH₃ H tert-butyl 2-F—C₆H₄ A.1783 H OCH₃ H tert-butyl 2-Cl—C₆H₄ A.1784 HOCH₃ H tert-butyl 2-CH₃—C₆H₄ A.1785 H OCH₃ H tert-butyl 2-CF₃—C₆H₄A.1786 H OCH₃ H tert-butyl 3-F—C₆H₄ A.1787 H OCH₃ H tert-butyl 3-Cl—C₆H₄A.1788 H OCH₃ H tert-butyl 3-CH₃—C₆H₄ A.1789 H OCH₃ H tert-butyl3-CF₃—C₆H₄ A.1790 H OCH₃ H tert-butyl 3-Br—C₆H₄ A.1791 H OCH₃ Htert-butyl 4-F—C₆H₄ A.1792 H OCH₃ H tert-butyl 4-Cl—C₆H₄ A.1793 H OCH₃ Htert-butyl 4-CH₃—C₆H₄ A.1794 H OCH₃ H tert-butyl 4-CF₃—C₆H₄ A.1795 HOCH₃ H tert-butyl 4-OCH₃—C₆H₄ A.1796 H OCH₃ H tert-butyl 4-OCF₃—C₆H₄A.1797 H OCH₃ H tert-butyl 4-Br—C₆H₄ A.1798 H OCH₃ H tert-butyl4-(CH═NOCH₃)—C₆H₄ A.1799 H OCH₃ H tert-butyl 4-(CH═NOEt)—C₆H₄ A.1800 HOCH₃ H tert-butyl 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1801 H OCH₃ H tert-butyl4-[C(CH₃)═NOEt]—C₆H₄ A.1802 H OCH₃ H tert-butyl 2,4-F₂—C₆H₃ A.1803 HOCH₃ H tert-butyl 2,4-Cl₂—C₆H₃ A.1804 H OCH₃ H tert-butyl2,4-(CH₃)₂—C₆H₃ A.1805 H OCH₃ H tert-butyl 3,5-F₂—C₆H₃ A.1806 H OCH₃ Htert-butyl 3,5-Cl₂—C₆H₃ A.1807 H OCH₃ H tert-butyl 3,5-(CH₃)₂—C₆H₃A.1808 H OCH₃ H tert-butyl 2-F-4-Cl—C₆H₃ A.1809 H OCH₃ H tert-butyl2-Cl-4-F—C₆H₃ A.1810 H OCH₃ H tert-butyl 3,4-F₂—C₆H₃ A.1811 H OCH₃ Htert-butyl 3,4-Cl₂—C₆H₃ A.1812 H OCH₃ H tert-butyl 2,3-F₂—C₆H₃ A.1813 HCF₃ H H C₆H₅ A.1814 H CF₃ H CH₃ C₆H₅ A.1815 H CF₃ H ethyl C₆H₅ A.1816 HCF₃ H n-propyl C₆H₅ A.1817 H CF₃ H n-butyl C₆H₅ A.1818 H CF₃ H isopropylC₆H₅ A.1819 H CF₃ H tert-butyl C₆H₅ A.1820 H CF₃ H H 4-F—C₆H₄ A.1821 HCF₃ H CH₃ 4-F—C₆H₄ A.1822 H CF₃ H ethyl 4-F—C₆H₄ A.1823 H CF₃ H n-propyl4-F—C₆H₄ A.1824 H CF₃ H n-butyl 4-F—C₆H₄ A.1825 H CF₃ H isopropyl4-F—C₆H₄ A.1826 H CF₃ H tert-butyl 4-F—C₆H₄ A.1827 H CH₃ CH₃ CH₃ CH₃A.1828 H CH₃ CH₃ CH₃ ethyl A.1829 H CH₃ CH₃ CH₃ n-propyl A.1830 H CH₃CH₃ CH₃ isopropyl A.1831 H CH₃ CH₃ CH₃ tert-butyl A.1832 H CH₃ CH₃ CH₃n-butyl A.1833 H CH₃ CH₃ CH₃ C₆H₅ A.1834 H CH₃ CH₃ CH₃ 2-F—C₆H₄ A.1835 HCH₃ CH₃ CH₃ 2-Cl—C₆H₄ A.1836 H CH₃ CH₃ CH₃ 2-CH₃—C₆H₄ A.1837 H CH₃ CH₃CH₃ 2-CF₃—C₆H₄ A.1838 H CH₃ CH₃ CH₃ 3-F—C₆H₄ A.1839 H CH₃ CH₃ CH₃3-Cl—C₆H₄ A.1840 H CH₃ CH₃ CH₃ 3-CH₃—C₆H₄ A.1841 H CH₃ CH₃ CH₃3-CF₃—C₆H₄ A.1842 H CH₃ CH₃ CH₃ 3-Br—C₆H₄ A.1843 H CH₃ CH₃ CH₃ 4-F—C₆H₄A.1844 H CH₃ CH₃ CH₃ 4-Cl—C₆H₄ A.1845 H CH₃ CH₃ CH₃ 4-CH₃—C₆H₄ A.1846 HCH₃ CH₃ CH₃ 4-CF₃—C₆H₄ A.1847 H CH₃ CH₃ CH₃ 4-OCH₃—C₆H₄ A.1848 H CH₃ CH₃CH₃ 4-OCF₃—C₆H₄ A.1849 H CH₃ CH₃ CH₃ 4-Br—C₆H₄ A.1850 H CH₃ CH₃ CH₃4-(CH═NOCH₃)—C₆H₄ A.1851 H CH₃ CH₃ CH₃ 4-(CH═NOEt)—C₆H₄ A.1852 H CH₃ CH₃CH₃ 4-[C(CH₃)═NOCH₃]—C₆H₄ A.1853 H CH₃ CH₃ CH₃ 4-[C(CH₃)═NOEt]—C₆H₄A.1854 H CH₃ CH₃ CH₃ 2,4-F₂—C₆H₃ A.1855 H CH₃ CH₃ CH₃ 2,4-Cl₂—C₆H₃A.1856 H CH₃ CH₃ CH₃ 2,4-(CH₃)₂—C₆H₃ A.1857 H CH₃ CH₃ CH₃ 3,5-F₂—C₆H₃A.1858 H CH₃ CH₃ CH₃ 3,5-Cl₂—C₆H₃ A.1859 H CH₃ CH₃ CH₃ 3,5-(CH₃)₂—C₆H₃A.1860 H CH₃ CH₃ CH₃ 2-F-4-Cl—C₆H₃ A.1861 H CH₃ CH₃ CH₃ 2-Cl-4-F—C₆H₃A.1862 H CH₃ CH₃ CH₃ 3,4-F₂—C₆H₃ A.1863 H CH₃ CH₃ CH₃ 3,4-Cl₂—C₆H₃A.1864 H CH₃ CH₃ CH₃ 2,3-F₂—C₆H₃ A.1865 H CH₃ CH₃ ethyl CH₃ A.1866 H CH₃CH₃ ethyl ethyl A.1867 H CH₃ CH₃ ethyl n-propyl A.1868 H CH₃ CH₃ ethylisopropyl A.1869 H CH₃ CH₃ ethyl tert-butyl A.1870 H CH₃ CH₃ ethyln-butyl A.1871 H CH₃ CH₃ ethyl C₆H₅ A.1872 H CH₃ CH₃ ethyl 2-F—C₆H₄A.1873 H CH₃ CH₃ ethyl 2-Cl—C₆H₄ A.1874 H CH₃ CH₃ ethyl 2-CH₃—C₆H₄A.1875 H CH₃ CH₃ ethyl 2-CF₃—C₆H₄ A.1876 H CH₃ CH₃ ethyl 3-F—C₆H₄ A.1877H CH₃ CH₃ ethyl 3-Cl—C₆H₄ A.1878 H CH₃ CH₃ ethyl 3-CH₃—C₆H₄ A.1879 H CH₃CH₃ ethyl 3-CF₃—C₆H₄ A.1880 H CH₃ CH₃ ethyl 3-Br—C₆H₄ A.1881 H CH₃ CH₃ethyl 4-F—C₆H₄ A.1882 H CH₃ CH₃ ethyl 4-Cl—C₆H₄ A.1883 H CH₃ CH₃ ethyl4-CH₃—C₆H₄ A.1884 H CH₃ CH₃ ethyl 4-CF₃—C₆H₄ A.1885 H CH₃ CH₃ ethyl4-OCH₃—C₆H₄ A.1886 H CH₃ CH₃ ethyl 4-OCF₃—C₆H₄ A.1887 H CH₃ CH₃ ethyl4-Br—C₆H₄ A.1888 H CH₃ CH₃ ethyl 4-(CH═NOCH₃)—C₆H₄ A.1889 H CH₃ CH₃ethyl 4-(CH═NOEt)—C₆H₄ A.1890 H CH₃ CH₃ ethyl 4-[C(CH₃)═NOCH₃]—C₆H₄A.1891 H CH₃ CH₃ ethyl 4-[C(CH₃)═NOEt]—C₆H₄ A.1892 H CH₃ CH₃ ethyl2,4-F₂—C₆H₃ A.1893 H CH₃ CH₃ ethyl 2,4-Cl₂—C₆H₃ A.1894 H CH₃ CH₃ ethyl2,4-(CH₃)₂—C₆H₃ A.1895 H CH₃ CH₃ ethyl 3,5-F₂—C₆H₃ A.1896 H CH₃ CH₃ethyl 3,5-Cl₂—C₆H₃ A.1897 H CH₃ CH₃ ethyl 3,5-(CH₃)₂—C₆H₃ A.1898 H CH₃CH₃ ethyl 2-F-4-Cl—C₆H₃ A.1899 H CH₃ CH₃ ethyl 2-Cl-4-F—C₆H₃ A.1900 HCH₃ CH₃ ethyl 3,4-F₂—C₆H₃ A.1901 H CH₃ CH₃ ethyl 3,4-Cl₂—C₆H₃ A.1902 HCH₃ CH₃ ethyl 2,3-F₂—C₆H₃ Et = ethyl

TABLE B No. X R³ R⁴ R^(a′) B. 1 N(COOCH₃)-OCH₃ H CH₃ H B. 2C(COOCH₃)═COCH₃ H CH₃ H B. 3 C(COOCH₃)═NOCH₃ H CH₃ H B. 4C(COOCH₃)═C-CH₃ H CH₃ H B. 5 C(CONHCH₃)═NOCH₃ H CH₃ H B. 6N(COOCH₃)-OCH₃ H C₆H₅ H B. 7 C(COOCH₃)═COCH₃ H C₆H₅ H B. 8C(COOCH₃)═NOCH₃ H C₆H₅ H B. 9 C(COOCH₃)═C-CH₃ H C₆H₅ H B. 10C(CONHCH₃)═NOCH₃ H C₆H₅ H B. 11 N(COOCH₃)-OCH₃ H 4-F-C₆H₄ H B. 12C(COOCH₃)═COCH₃ H 4-F-C₆H₄ H B. 13 C(COOCH₃)═NOCH₃ H 4-F-C₆H₄ H B. 14C(COOCH₃)═C-CH₃ H 4-F-C₆H₄ H B. 15 C(CONHCH₃)═NOCH₃ H 4-F-C₆H₄ H B. 16N(COOCH₃)-OCH₃ H CH₃ CH₃ B. 17 C(COOCH₃)═COCH₃ H CH₃ CH₃ B. 18C(COOCH₃)═NOCH₃ H CH₃ CH₃ B. 19 C(COOCH₃)═C-CH₃ H CH₃ CH₃ B. 20C(CONHCH₃)═NOCH₃ H CH₃ CH₃ B. 21 N(COOCH₃)-OCH₃ H C₆H₅ CH₃ B. 22C(COOCH₃)═COCH₃ H C₆H₅ CH₃ B. 23 C(COOCH₃)═NOCH₃ H C₆H₅ CH₃ B. 24C(COOCH₃)═C-CH₃ H C₆H₅ CH₃ B. 25 C(CONHCH₃)═NOCH₃ H C₆H₅ CH₃ B. 26N(COOCH₃)-OCH₃ H 4-F-C₆H₄ CH₃ B. 27 C(COOCH₃)═COCH₃ H 4-F-C₆H₄ CH₃ B. 28C(COOCH₃)═NOCH₃ H 4-F-C₆H₄ CH₃ B. 29 C(COOCH₃)═C-CH₃ H 4-F-C₆H₄ CH₃ B.30 C(CONHCH₃)═NOCH₃ H 4-F-C₆H₄ CH₃ B. 31 N(COOCH₃)-OCH₃ CH₃ CH₃ H B. 32C(COOCH₃)═COCH₃ CH₃ CH₃ H B. 33 C(COOCH₃)═NOCH₃ CH₃ CH₃ H B. 34C(COOCH₃)═C-CH₃ CH₃ CH₃ H B. 35 C(CONHCH₃)═NOCH₃ CH₃ CH₃ H B. 36N(COOCH₃)-OCH₃ CH₃ C₆H₅ H B. 37 C(COOCH₃)═COCH₃ CH₃ C₆H₅ H B. 38C(COOCH₃)═NOCH₃ CH₃ C₆H₅ H B. 39 C(COOCH₃)═C-CH₃ CH₃ C₆H₅ H B. 40C(CONHCH₃)═NOCH₃ CH₃ C₆H₅ H B. 41 N(COOCH₃)-OCH₃ CH₃ 4-F-C₆H₄ H B. 42C(COOCH₃)═COCH₃ CH₃ 4-F-C₆H₄ H B. 43 C(COOCH₃)═NOCH₃ CH₃ 4-F-C₆H₄ H B.44 C(COOCH₃)═C-CH₃ CH₃ 4-F-C₆H₄ H B. 45 C(CONHCH₃)═NOCH₃ CH₃ 4-F-C₆H₄ HB. 46 N(COOCH₃)-OCH₃ CH₃ CH₃ CH₃ B. 47 C(COOCH₃)═COCH₃ CH₃ CH₃ CH₃ B. 48C(COOCH₃)═NOCH₃ CH₃ CH₃ CH₃ B. 49 C(COOCH₃)═C-CH₃ CH₃ CH₃ CH₃ B. 50C(CONHCH₃)═NOCH₃ CH₃ CH₃ CH₃ B. 51 N(COOCH₃)-OCH₃ CH₃ C₆H₅ CH₃ B. 52C(COOCH₃)═COCH₃ CH₃ C₆H₅ CH₃ B. 53 C(COOCH₃)═NOCH₃ CH₃ C₆H₅ CH₃ B. 54C(COOCH₃)═C-CH₃ CH₃ C₆H₅ CH₃ B. 55 C(CONHCH₃)═NOCH₃ CH₃ C₆H₅ CH₃ B. 56N(COOCH₃)-OCH₃ CH₃ 4-F-C₆H₄ CH₃ B. 57 C(COOCH₃)═COCH₃ CH₃ 4-F-C₆H₄ CH₃B. 58 C(COOCH₃)═NOCH₃ CH₃ 4-F-C₆H₄ CH₃ B. 59 C(COOCH₃)═C-CH₃ CH₃4-F-C₆H₄ CH₃ B. 60 C(CONHCH₃)═NOCH₃ CH₃ 4-F-C₆H₄ CH₃

TABLE C No. X R² R³ R⁴ R^(a) C. 1 N(COOCH₃)-OCH₃ H H CH₃ H C. 2C(COOCH₃)═COCH₃ H H CH₃ H C. 3 C(COOCH₃)═NOCH₃ H H CH₃ H C. 4C(COOCH₃)═C-CH₃ H H CH₃ H C. 5 C(CONHCH₃)═NOCH₃ H H CH₃ H C. 6N(COOCH₃)-OCH₃ H H C₆H₅ H C. 7 C(COOCH₃)═COCH₃ H H C₆H₅ H C. 8C(COOCH₃)═NOCH₃ H H C₆H₅ H C. 9 C(COOCH₃)═C-CH₃ H H C₆H₅ H C. 10C(CONHCH₃)═NOCH₃ H H C₆H₅ H C. 11 N(COOCH₃)-OCH₃ H H 4-F-C₆H₄ H C. 12C(COOCH₃)═COCH₃ H H 4-F-C₆H₄ H C. 13 C(COOCH₃)═NOCH₃ H H 4-F-C₆H₄ H C.14 C(COOCH₃)═C-CH₃ H H 4-F-C₆H₄ H C. 15 C(CONHCH₃)═NOCH₃ H H 4-F-C₆H₄ HC. 16 N(COOCH₃)-OCH₃ H CH₃ CH₃ CH₃ C. 17 C(COOCH₃)═COCH₃ H CH₃ CH₃ CH₃C. 18 C(COOCH₃)═NOCH₃ H CH₃ CH₃ CH₃ C. 19 C(COOCH₃)═C-CH₃ H CH₃ CH₃ CH₃C. 20 C(CONHCH₃)═NOCH₃ H CH₃ CH₃ CH₃ C. 21 N(COOCH₃)-OCH₃ H CH₃ C₆H₅ CH₃C. 22 C(COOCH₃)═COCH₃ H CH₃ C₆H₅ CH₃ C. 23 C(COOCH₃)═NOCH₃ H CH₃ C₆H₅CH₃ C. 24 C(COOCH₃)═C-CH₃ H CH₃ C₆H₅ CH₃ C. 25 C(CONHCH₃)═NOCH₃ H CH₃C₆H₅ CH₃ C. 26 N(COOCH₃)-OCH₃ H CH₃ 4-F-C₆H₄ CH₃ C. 27 C(COOCH₃)═COCH₃ HCH₃ 4-F-C₆H₄ CH₃ C. 28 C(COOCH₃)═NOCH₃ H CH₃ 4-F-C₆H₄ CH₃ C. 29C(COOCH₃)═C-CH₃ H CH₃ 4-F-C₆H₄ CH₃ C. 30 C(CONHCH₃)═NOCH₃ H CH₃ 4-F-C₆H₄CH₃ C. 31 N(COOCH₃)-OCH₃ H CH₃ C₆H₅ ethyl C. 32 C(COOCH₃)═COCH₃ H CH₃C₆H₅ ethyl C. 33 C(COOCH₃)═NOCH₃ H CH₃ C₆H₅ ethyl C. 34 C(COOCH₃)═C-CH₃H CH₃ C₆H₅ ethyl C. 35 C(CONHCH₃)═NOCH₃ H CH₃ C₆H₅ ethyl

The compounds I are suitable as fungicides. They have excellent activityagainst a broad spectrum of phytopathogenic fungi, in particular fromthe classes of the Ascomycetes, Deuteromycetes, Phycomycetes andBasidiomycetes. Some of them act systemically and can be employed incrop protection as foliar- and soil-acting fungicides.

They are especially important for controling a large number of fungi ina variety of crop plants such as wheat, rye, barley, oats, rice, maize,grass, bananas, cotton, soya, coffee, sugar cane, grape vines, fruitspecies, ornamentals and vegetable species such as cucumbers, beans,tomatoes, potatoes and cucurbits, and also in the seeds of these plants.

Specifically, they are suitable for controling the following plantdiseases:

Alternaria species in vegetables and fruit,

Botrytis cinerea (gray mold) in strawberries, vegetables, ornamentalsand grape vines,

Cercospora arachidicola in groundnuts,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Erysiphe graminis (powdery mildew) in cereals,

Fusarium and Verticillium species in a variety of plants,

Helminthosporium species in cereals,

Mycosphaerella species in bananas,

Phytophthora infestans in potatoes and tomatoes,

Plasmopara viticola in grape vines,

Podosphaera leucotricha in apples,

Pseudocercosporella herpotrichoides in wheat and barley,

Pseudoperonospora species in hops and cucumbers,

Puccinia species in cereals,

Pyricularia oryzae in rice,

Rhizoctonia species in cotton, rice and lawns,

Septoria nodorum in wheat,

Uncinula necator in grape vines,

Ustilago species in cereals and sugar cane, and

Venturia inaequalis (scab) in apples.

The compounds I are also suitable for controling harmful fungi such asPaecilomyces variotii in the protection of materials (for example wood,paper, paint dispersions, fibers or tissues) and in the protection ofstored products.

The compounds I are employed by treating the fungi or the plants, seeds,materials or the soil to be protected against fungal attack with afungicidally effective amount of the active compounds. The applicationis carried out before or after the infection of the materials, plants orseeds by the fungi.

The fungicidal compositions generally comprise from 0.1 to 95,preferably from 0.5 to 90, % by weight of active compound.

For use in crop protection, the application rates are, depending on thekind of effect desired, from 0.01 to 2.0 kg of active compound per ha.

The treatment of seeds generally requires active compound quantities offrom 0.001 to 0.1 g, preferably from 0.01 to 0.05 g, per kilogram ofseed.

For use in the protection of materials or stored products, the activecompound application rate depends on the kind of application area andeffect desired. Customary application rates in the protection ofmaterials are, for example, from 0.001 g to 2 kg, preferably from 0.005g to 1 kg, of active compound per cubic meter of treated material.

The compounds of the formula I are also suitable for the efficientcontrol of animal pests from the classes of the insects, arachnids andnematodes. They can be used for controling animal pests in cropprotection and in the sectors of hygiene, protection of stored productsand in the veterinary sector. They are particularly suitable forcontroling the following animal pests:

Insects from the order of the lepidopterons (Lepidoptera), for exampleAgrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsiagemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius,Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneurafumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydiapomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella,Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella,Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholithafunebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens,Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea,Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria,Laphygma exigua, Leucoptera coffeella, Leucoptera scitella,Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis,Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosomaneustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis,Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalerabucephala, Phthorimaea operculella, Phyllocnistis citrella, Pierisbrassicae, Plathypena scabra, Plutella xylostella, Pseudoplusiaincludens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotrogacerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodopteralittoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrixviridana, Trichoplusia ni and Zeiraphera canadensis,

beetles (Coleoptera), eg. Agrilus sinuatus, Agriotes lineatus, Agriotesobscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomusgrandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda,Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis,Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata,Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis,Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis,Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis,Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis,Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata,Lema melanopus, Leptinotarsa decemlineata, Limonius californicus,Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus,Melolontha hippocastani, Melolontha melolontha, Oulema oryzae,Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae,Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola,Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitonalineatus and Sitophilus granaria,

dipterons (Diptera), eg. Aedes aegypti, Aedes vexans, Anastrepha ludens,Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana,Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola,Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae,Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis,Glossina morsitans, Haematobia irritans, Haplodiplosis equestris,Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyzatrifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoriapectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans,Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua,Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletispomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa,

thrips (Thysanoptera), eg. Frankliniella fusca, Frankliniellaoccidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae,Thrips palmi and Thrips tabaci,

hymenopterons (Hymenoptera), eg. Athalia rosae, Atta cephalotes, Attasexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea,Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,

heteropterons (Heteroptera), eg. Acrosternum hilare, Blissusleucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercusintermedius, Eurygaster integriceps, Euschistus impictiventris,Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezaraviridula, Piesma quadrata, Solubea insularis and Thyanta perditor,

homopterons (Homoptera), eg. Acyrthosiphon onobrychis, Adelges laricis,Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycauduscardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusianordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthumpseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphumeuphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum,Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius,Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri,Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala,Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa,Trialeurodes vaporariorum and Viteus vitifolii,

termites (Isoptera), eg. Calotermes flavicollis, Leucotermes flavipes,Reticulitermes lucifugus and Termes natalensis,

orthopterons (Orthoptera), eg. Acheta domestica, Blatta orientalis,Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa,Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum,Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus,Nomadacris septemfasciata, Periplaneta americana, Schistocercaamericana, Schistocerca peregrina, Stauronotus maroccanus and Tachycinesasynamorus,

Arachnoidea such as arachnids (Acarina), eg. Amblyomma americanum,Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilusdecoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobiapraetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyessheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus,Ornithodorus moubata, Otobius megnini, Paratetranychus pilosus,Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemuslatus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalusevertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychuskanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychusurticae,

nematodes such as root ball nematodes, eg. Meloidogyne hapla,Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg.Globodera rostochiensis, Heterodera avenae, Heterodera glycines,Heterodera schachtii, Heterodera trifolii, stem and leaf nematodes, eg.Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci,Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis,Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni,Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans,Pratylenchus curvitatus and Pratylenchus goodeyi.

For controling animal pests under free range conditions, the applicationrate of active compound is from 0.1 to 2.0, preferably 0.2 to 1.0,kg/ha.

The compounds I can be converted into the customary formulations, eg.solutions, emulsions, suspensions, dusts, powders, pastes and granules.The use form depends on the specific intended use; in any case, itshould guarantee fine and uniform distribution of the compound accordingto the invention.

The formulations are prepared in a known manner, eg. by extending theactive compound with solvents and/or carriers, if desired usingemulsifiers and dispersants, it being possible to use other organicsolvents as auxiliary solvents if water is used as the diluent. Suitableauxiliaries for this purpose are essentially: solvents such as aromatics(eg. xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg.mineral oil fractions), alcohols (eg. methanol, butanol), ketones (eg.cyclohexanone), amines (eg. ethanolamine, dimethylformamide) and water;carriers such as ground natural minerals (eg. kaolin, clays, talc,chalk) and ground synthetic minerals (eg. finely divided silica,silicates); emulsifiers such as nonionic and anionic emulsifiers (eg.polyoxyethylene fatty alcohol ethers, alkylsulfonates andarylsulfonates), and dispersants such as lignin-sulfite waste liquorsand methylcellulose.

Suitable surfactants are the alkali metal, alkaline earth metal andammonium salts of lignosulfonic acid, naphthalenesulfonic acid,phenolsulfonic acid, and dibutylnaphthalenesulfonic acid,alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcoholsulfates and fatty acids and alkali metal salts and alkaline earth metalsalts thereof, salts of sulfated fatty alcohol glycol ethers,condensation products of sulfonated naphthalene and naphthalenederivatives with formaldehyde, condensation products of naphthalene orof naphthalene sulfonic acid with phenol and formaldehyde,polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol,octylphenol and nonylphenol, alkylphenol polyglycol ethers,tributylphenyl polyglycol ethers, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylatedpolyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitolesters, lignin-sulfite waste liquors and methylcellulose.

Suitable for preparing directly sprayable solutions, emulsions, pastesor oil dispersions are petroleum fractions having medium to high boilingpoints, such as kerosine or diesel fuel, furthermore coal-tar oils andoils of plant or animal origin, aliphatic, cyclic and aromatichydrocarbons, for example benzene, toluene, xylene, paraffin,tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof,methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride,cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polarsolvents, for example dimethylformamide, dimethyl sulfoxide,N-methylpyrrolidone, and water.

Powders, compositions for broadcasting and dusts can be prepared bymixing or joint grinding the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules andhomogenous granules, can be prepared by binding the active compounds tosolid carriers. Solid carriers are, for example, mineral earths, such assilica gel, silicas, silicates, talc, kaolin, attaclay, limestone, lime,chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate,magnesium sulfate, magnesium oxide, ground synthetic materials,fertilizers, such as ammonium sulfate, ammonium phosphate, ammoniumnitrate, ureas and products of vegetable origin, such as cereal meal,tree bark meal, wood meal and nutshell meal, cellulose powders and othersolid carriers.

The formulations generally comprise from 0.01 to 95% by weight,preferably from 0.1 to 90% by weight, of the active compound. The activecompounds are employed in a purity of from 90% to 100%, preferably from95% to 100% (according to the NMR spectrum).

Examples of formulations are:

I. 5 parts by weight of a compound according to the invention arethoroughly mixed with 95 parts by weight of finely divided kaolin. Thisaffords a dusting composition comprising 5% by weight of the activecompound.

II. 30 parts by weight of a compound according to the invention arethoroughly mixed with a mixture of 92 parts by weight of pulverulentsilica gel and 8 parts by weight of paraffin oil which had been sprayedonto the surface of this silica gel. This affords an active compoundpreparation having good adhesive properties (active compound content 23%by weight).

III. 10 parts by weight of a compound according to the invention aredissolved in a mixture comprising 90 parts by weight of xylene, 6 partsby weight of the addition product of 8 to 10 mol of ethylene oxide to 1mol of oleic acid N-monoethanolamide, 2 parts by weight of the calciumsalt of dodecylbenzenesulfonic acid and 2 parts by weight of theaddition product of 40 mol of ethylene oxide to 1 mol of castor oil(active compound content 9% by weight).

IV. 20 parts by weight of a compound according to the invention aredissolved in a mixture comprising 60 parts by weight of cyclohexanone,30 parts by weight of isobutanol, 5 parts by weight of the additionproduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 5parts by weight of the addition product of 40 mol of ethylene oxide to 1mol of castor oil (active compound content 16% by weight).

V. 80 parts by weight of a compound according to the invention are mixedwell with 3 parts by weight of the sodium salt ofdiisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodiumsalt of a lignosulfonic acid from a sulfite waste liquor and 7 parts byweight of pulverulent silica gel, and ground in a hammer mill (activecompound content 80% by weight).

VI. 90 parts by weight of a compound according to the invention aremixed with 10 parts by weight of N-methyl-α-pyrrolidone, affording asolution which is suitable for use in the form of very small drops(active compound content 90% by weight).

VII. 20 parts by weight of a compound according to the invention aredissolved in a mixture comprising 40 parts by weight of cyclohexanone,30 parts by weight of isobutanol, 20 parts by weight of the additionproduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10parts by weight of the addition product of 40 mol of ethylene oxide to 1mol of castor oil. The solution is poured into 100,000 parts by weightof water and finely dispersed therein, affording an aqueous dispersioncomprising 0.02% by weight of active compound.

VIII. 20 parts by weight of a compound according to the invention aremixed well with 3 parts by weight of the sodium salt ofdiisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodiumsalt of a lignosulfonic acid from a sulfite waste liquor and 60 parts byweight of pulverulent silica gel, and ground in a hammer mill. Themixture is finely dispersed in 20,000 parts by weight of water,affording a spray liquor comprising 0.1% by weight of active compound.

The active compounds can be applied as such, in the form of theirformulations or in the application forms prepared therefrom, for examplein the form of directly sprayable solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dusts, compositions forbroadcasting, or granules, by spraying, atomizing, dusting, broadcastingor watering. The application forms depend entirely on the intended uses;in any case, they should guarantee very fine dispersion of the activecompounds according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes orwettable powders (spray powders, oil dispersions) by addition of water.To prepare emulsions, pastes or oil dispersions, the substances can behomogenized in water as such or dissolved in an oil or solvent, by meansof wetting agents, tackifiers, dispersants or emulsifiers. However,concentrates comprising active compound, wetting agent, tackifier,dispersant or emulsifier and possibly solvent or oil which are suitablefor dilution with water can also be prepared.

The active compound concentrations in the ready-to-use preparations canbe varied over a relatively wide range. In general, they are from 0.0001to 10%, preferably from 0.01 to 1%.

It is also possible to use the active compounds with good success in theultra-low-volume method (ULV), it being possible to apply formulationscomprising more than 95% by weight of active compound or even the activecompound without additives.

Oils of various types, herbicides, fungicides, other pesticides andbactericides can be added to the active compounds, if desired evenimmediately prior to application (tank mix). These agents can be addedto the compositions according to the invention in a weight ratio of 1:10to 10:1.

The compositions according to the invention in the use form asfungicides may also be present in combination with other activecompounds, for example with herbicides, insecticides, growth regulators,fungicides or else with fertilizers. In many cases, a mixture of thecompounds I, or of the compositions comprising them, in the use form asfungicides with other fungicides results in a broader fungicidalspectrum of activity.

The following list of fungicides in combination with which the compoundsaccording to the invention can be used is intended to illustrate thepossible combinations, but not to impose any limitation:

sulfur, dithiocarbamates and their derivatives, such as iron(III)dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinkethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate,manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuramdisulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate),ammonia complex of zinc (N,N′-propylenebisdithiocarbamate), zinc(N,N′-propylenebisdithiocarbamate),N,N′-polypropylenebis(thiocarbamoyl)disulfide;

nitro derivatives, such as dinitro-(1-methylheptyl)phenyl crotonate,2-sec-butyl-4,6-dinitrophenyl-3,3-dimethyl acrylate,2-sec-butyl-4,6-dinitrophenylisopropyl carbonate, diisopropyl5-nitroisophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate,2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethylphthalimidophosphonothioate,5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole,2,3-dicyano-1,4-dithioanthraquinone,2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl1-(butylcarbamoyl)-2-benzimidazolecarbamate,2-methoxycarbonylaminobenzimidazole, 2-(furyl-(2))benzimidazole,2-(thiazolyl-(4))benzimidazole,N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide,N-trichloromethylthiotetrahydrophthalimide,N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfuric diamide,5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene,4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine2-thio-1-oxide, 8-hydroxyquinoline or its copper salt,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine-4,4-dioxide,2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide,2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide,2,4,5-trimethylfuran-3-carboxanilide,N-cyclohexyl-2,5-dimethylfuran-3-carboxamide,N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide,2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine2,2,2-trichloroethyl acetal,piperazine-1,4-diyl-bis-1-(2,2,2-trichloroethyl)formamide,1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,2,6-dimethyl-N-tridecylmorpholine or its salts,2,6-dimethyl-N-cyclododecylmorpholine or its salts,N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine,N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine,1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole,1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N′-imidazolylurea,1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone,1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol,(2RS,3RS)-1-(3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-ylmethyl-1H-1,2,4-triazole,α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine,bis(p-chlorophenyl)-3-pyridinemethanol,1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene,1,2-bis-(3-methoxycarbonyl-2-thioureido)benzene

strobilurins, such as methylE-methoximino-[α-(o-tolyloxy)-o-tolyl]acetate, methylE-2-{2-[6-(2-cyanophenoxy)-pyridimin-4-yloxy]-phenyl}-3-methoxyacrylate,N-methyl E-methoximino-[α-(2-phenoxyphenyl)]acetamide,methyl-E-methoximino-[α-(2,5-dimethylphenoxy)-o-tolyl]acetamide,

anilinopyrimidines, such as N-(4,6-dimethylpyrimidin-2-yl)aniline,N-[4-methyl-6-(1-propynyl)pyrimidin-2-yl]aniline,N-(4-methyl-6-cyclopropylpyrimidin-2-yl)aniline,

phenylpyrroles, such as4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile,

cinnamamides, such as3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloylmorpholine.

and a variety of fungicides, such as dodecylguanidine acetate,3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide,hexachlorobenzene, methylN-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate,DL-N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)alanine methyl ester,N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone,DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester,5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,3-(3,5-dichlorophenyl)-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin,N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]acetamide,1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole,2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol,N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine,1-((bis-(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.

Preference is given to the fungicidal activity.

SYNTHESIS EXAMPLES

The procedures given in the synthesis examples below were used to obtainfurther compounds I by appropriate modification of the startingmaterials. The compounds obtained in this manner are listed in thetables that follow, together with physical data.

Example 1 Preparation of 2,2-dimethoxy-1-phenylpropan-1-one

1.2 g of trimethoxymethane and 8.7 ml of 25% strength by weightethanolic HCl solution were added to 14.8 g of 1-phenylpropane-1,2-dionedissolved in 27.5 ml of methanol. The reaction mixture was stirred at 20to 25° C. for 2 hours, and the solvent was then removed by distillation.The residue was taken up in methyl tert-butyl ether (MTBE) and thesolution was washed with water. The organic phases were dried and thesolvent removed by distillation. 18.2 g of product were obtained as aclear oil.

¹H NMR (CDCl₃): 2.6 (s, 3H); 3.3 (s, 6H); 7.4-7.6 (m, 3H); 8.2 ppm (m,2H).

Example 2 Preparation of [1-(1,1-dimethoxyethyl)propenyl]benzene

At 5° C., a solution of 2.5 g of potassium tert-butoxide in 25 ml oftetrahydrofuran (THF) was added dropwise to 8.2 g ofethyltriphenylphosphonium bromide dissolved in 50 ml of THF. The mixturewas then stirred at 5° C. for about 10 min, and a solution of 3.9 g of2,2-dimethoxy-1-phenylpropan-1-one from Example 1 in 10 ml of THF wasadded dropwise. The reaction mixture was stirred at 20 to 25° C. for 72h and then admixed with about 300 ml of water and extracted with methyltert-butyl ether (MTBE). The organic phases were washed with water,dried and freed of the solvent. Silica gel chromatography(MTBE/cyclohexane 1:10) of the residue gave 2.2 g of product as anisomer mixture which can be further reacted without purification.

Example 3 Preparation of 3-phenylpent-3-ene 2-oxime

15.5 g of hydroxylammonium hydrochloride and 17.6 g of pyridine wereinitially charged in 140 ml of methanol. A solution of 30.7 g of the[1-(1,1-dimethoxyethyl)propenyl]benzene obtained from Example 2 in 140ml of methanol was added dropwise and the mixture is stirred at 20 to25° C. for 72 h. The reaction mixture was taken up in about 1.5 litersof NaCl solution and extracted with methyl tert-butyl ether (MTBE). Theorganic phases were washed with 5% strength by weight of hydrochloricacid and then with water. After drying and removal of the solvent bydistillation, this gave 14.5 g of product as a light-yellow powder ofmp. 99-101°C.

¹H NMR (CDCl₃): 1.6 (d, 3H); 2.0 (s,3H); 6.2 (q, 1H); 7.0-7.4 (m, 5H);8.5 ppm (s, 1H).

Example 4 Preparation of methyl(E)-2-methoxyimino-2-(3-phenylpent-3-ene-2-iminooxymethyl)phenylacetate

25 g (142 mmol) of the oxime obtained from Example 3 dissolved in 100 mlof dimethylformamide (DMF) were admixed with 25 g of 30% strength byweight of a methanolic sodium methoxide solution. The mixture wasstirred at 20 to 25° C. for 15 min and then 40.8 g (142 mmol) of methyl2-bromomethylphenylglyoxylate O-methyloxime dissolved in 100 ml of DMFwere added dropwise. The reaction mixture was stirred at 20 to 25° C.for about 3 h, poured into ice-water and extracted with methyltert-butyl ether (MTBE). The organic phases were washed, dried and freedof the solvent. Silica gel chromatography (MTBE/cyclohexane 1:9) of theresidue gave 32 g of the title compound.

¹H NMR (CDCl₃): 1.6 (d, 3H); 3.8 (s, 3H); 4.0 (s, 3H); 5.0 (s, 2H); 6.2(q, 1H); 7.1-7.5 ppm (m, 9H).

Example 5 Preparation of(E)-2-methoxyimino-2-[(3-phenyl)pent-3-ene-2-iminooxymethyl]phenyl-N-methylacetamide

12.4 g (32.6 mmol) of the ester obtained from Example 4 were dissolvedin 200 ml of tetrahydrofuran (THF), and 25.3 g of a 40% strength byweight aqueous methylamine solution were added dropwise. The solutionwas stirred at 20 to 25° C. for 2 h, poured into ice-water and extractedwith methyl tert-butyl ether (MTBE). The organic phases were washed,dried and freed of the solvent. Silica gel chromatography(MTBE/cyclohexane 1:3) of the residue gave 7.7 g of product.

¹H NMR (CDCl₃): 1.6 (d, 3H); 1.8 (s, 3H); 2.85 (d, 3H); 3.9 (s, 3H);4.95 (s, 2H); 6.1 (q, 1H); 6.7 (s, 1H); 7.1-7.5 ppm (m, 9H).

Example 6 Preparation of(E)-2-methoxyimino-2-[1-(3-methyl-2-phenyloxiranyl)ethylideneiminooxymethyl]phenyl-N-methylacetamide

20.3 g (53.6 mmol) of the amide obtained from Example 5 were dissolvedin 250 ml of methylene chloride. 24.4 g (77.7 mmol) of3-chloroperbenzoic acid were added and the reaction mixture was stirredat 20 to 25° C. for 18 h. The reaction mixture was poured into water andwashed with sodium thiosulfate and sodium hydroxide solution and thenwith water. The organic phase was separated off, dried and freed of thesolvent. Silica gel chromatography (MTBE/cyclohexane 1:3) of the residuegave 21.3 g of the product as an oil.

¹H NMR (CDCl₃): 1.0 (d, 3H); 1.8 (s, 3H); 2.8 (d, 3H); 3.7 (q, 1H); 4.0(s, 3H); 5.0 (s, 2H); 6.7 (s, 1H); 6.7 (s, 1H); 7.2-7.5 ppm (m, 9H).

Example 7 Preparation of methyl(E)-2-methoxyimino-2-[1-(1-phenylcyclopropyl)ethylideneiminooxymethyl]phenylacetate

A solution of 3.5 g of 1-(1-phenylcyclopropyl)ethylidene oxime in 10 mlof DMF was added dropwise to 0.53 g of sodium hydride in 30 ml ofanhydrous dimethylformamide (DMF). The mixture was stirred at 60° C. for2 hours and 4.2 g of methyl 2-bromomethylphenylglyoxylate dissolved in20 ml of DMF were then added dropwise at 0° C. The solution was stirredat 20 to 25° C. overnight, poured into ice-water and extracted withmethyl tert-butyl ether (MTBE). The organic phases were washed, driedand freed of the solvent. Silica gel chromatography (toluene) of theresidue gave 3 g of the title compound as yellow crystals of mp. 67-70°C.

¹H NMR (CDCl₃): 0.9 (m, 2H); 1.2 (m, 2H); 1.8 (s, 3H); 3.8 (s, 3H); 4.0(s, 3H); 5.0 (s, 2H); 7.1-7.6 (m, 9H).

TABLE I

I.1: X = N(COOCH₃)—OCH₃ I.2: X = C(COOCH₃)═CH—OCH₃ I.3: X =C(COOCH₃)═N—OCH₃ I.4: X = C(CONHCH₃)═N—OCH₃ I.5: X = C(COOCH₃)═CH—CH₃Phys. data (Mp.[° C.], IR [cm⁻¹], ¹H NMR No. X Y Z R² R⁴ [ppm/CDCl₃]) 1I.4 H O CH₃ C₆H₅ 1,0 (3H); 1.7 (3H); 2.95 (3H); 3.7 (1H); 4.0 (3H); 5.0(2H); 6.7 (NH) 2 I.1 H O CH₃ C₆H₅ 1.0 (3H); 1.8 (3H) 3.7 (3H); 3.8 (3H);5.2 (2H); 7.2-7.5 (9H) 3 I.4 H O CH₃ CH₃ 1.3 (3H); 1.4 (3H); 1.6 (3H);2.95 (3H); 3.1 (1H); 4.0 (3H); 5.0 (2H) 4 I.4 H O C₆H₅ CH₃ 1673, 1526,1037, 979 5 I.3 H CH₂ H C₆H₅ 67-70 6 I.4 H CH₂ H C₆H₅ 0.9 (2H); 1.2(2H); 1.8 (3H); 2.8 (3H); 4.0 (3H); 5.0 (2H); 6.8 (NH); 7.1-7.6 (9H) 7I.3 H CH₂ H 4-Cl—C₆H₄ 0.95 (2H); 1.25 (2H); 1.8 (3H); 3.8 (3H); 4.05(3H); 5.0 (2H); 7.1-7.4 (8H) 8 I.4 H CH₂ H 4-Cl—C₆H₄ 0.9 (2H); 1.25(2H); 1.8 (3H); 2.85 (3H); 3.9 (3H); 4.9 (2H); 6.6 (NH); 7.1-7.4 (8H) 91.3 H O —CH₂CH₃ C₆H₅ 1729, 1449, 1219, 1970 10 1.4 H O —CH₂CH₃ C₆H₅1675, 1525, 1449, 1038 11 1.1 H O —CH₂CH₃ C₆H₅ 1740, 1440, 1335, 1028 121.3 H O —CH₂CH₂CH₃ C₆H₅ 1729, 1449, 1219, 1070 13 1.4 H O —CH₂CH₂CH₃C₆H₅ 1674, 1525, 1448, 1058 14 1.1 H O —CH₂CH₂CH₃ C₆H₅ 1740, 1441, 1337,1105 15 1.3 H O —CH₂CH₂CH₂CH₃ C₆H₅ 1729, 1448, 1219, 1070 16 1.4 H O—CH₂CH₂CH₂CH₃ C₆H₅ 1674, 1524, 1448, 1038 17 1.1 H O —CH₂CH₂CH₂CH₃ C₆H₅1740, 1441, 1336, 1195 18 1.3 H O —CH₃ 4-F—C₆H₄ 1728, 1508, 1221, 197019 1.4 H O —CH₃ 4-F—C₆H₄ 1673, 1509, 1222, 1937

Examples of the Activity Against Harmful Fungi

The fungicidal activity of the compounds of the formula I wasdemonstrated by the following experiments:

The active compounds were prepared as a 10% strength emulsion in amixture of 63% by weight of cyclohexanone and 27% by weight ofemulsifier and diluted with water to the desired concentration.

The compounds A and B, known from EP-A 463 488 as Nos. 56 of Tables Iand II, served as comparative active compounds:

Use Example 1—Activity Against Powdery Mildew of Wheat

Leaves of wheat seedlings cv. “Frühgold” in pots were sprayed to runoffpoint with an aqueous active compound preparation and, 24 hours afterthe spray coating had dried on, dusted with spores of powdery mildew ofwheat (Erysiphe graminis forma specialis tritici). The test plants weresubsequently placed in a greenhouse at from 20 to 22° C. and a relativeatmospheric humidity of 75 to 80%. After 7 days, the extent of mildewdevelopment was determined visually as % infestation of the total leafarea.

In this test, the plants treated with 16 ppm of the compounds Nos. 1, 2,3, 4, 9, 10, 11, 12, 13, 14 and 18 of Table I showed an infestation ofno more than 15%, while the plants treated with 16 ppm of thecomparative compounds A and B and the untreated plants showed aninfestation of 40% and 80%, respectively.

Use Example 2 —Activity Against Plasmopara viticola

Leaves of potted vines cv. “Müller-Thurgau” were sprayed to runoff pointwith an aqueous active compound preparation. To assess the persistencyof the substances, the plants were kept for 7 days in a greenhouse afterthe spray coating had dried on. Only then were the leaves inoculatedwith an aqueous zoospore suspension of Plasmopara viticola. The grapevines were then initially kept in a water vapor-saturated chamber at 24°C. for 48 hours and then in a greenhouse at 20-30° C. for 5 days. Afterthis, the plants were once more kept in a humid chamber for 16 hours topromote sporangiophore eruption. The extent of the infestation on theundersides of the leaves was then assessed visually.

In this test, the plants treated with 16 ppm of the compounds Nos. 1, 4,5, 6, 7, 8, 9, 10, 12, 13, 16, 18 and 19 of Table I showed a maximuminfestation of 10%, while the plants treated with 16 ppm of comparativecompound B and the untreated plants showed an infestation of 60% and80%, respectively.

Use Example 3 —Activity Against Pyricularia oryzae (protective)

Leaves of potted rice seedlings cv. “Tai-Nong 67” were sprayed to runoffpoint with an aqueous active compound preparation. The next day, theplants were inoculated with an aqueous spore suspension of Pyriculariaoryzae. The test plants were subsequently kept in climatized chambers at22-24° C. and 95-99% relative atmospheric humidity for 6 days. Theextent of the infestation of the leaves was then determined visually.

In this test, the plants treated with 16 ppm of the compounds Nos. 1, 2,4, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 18 and 19 of Table I showed amaximum infestation of 15%, while the plants treated with 16 ppm ofcomparative compound B and the untreated plants showed an infestation of40% and 80%, respectively.

Examples of the Activity Against Animal Pests

The activity of the compounds of the formula I against animal pests wasdemonstrated by the following experiments:

The active compounds were prepared

a. as a 0.1% strength solution in acetone or

b. as a 10% strength emulsion in a mixture of 70% by weight ofcyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wettingagent having emulsifier and dispersant action based on ethoxylatedalkylphenols) and 10% by weight of Wettol® EM (nonionic emulsifier basedon ethoxylated castor oil)

and diluted with acetone in the case of a. or with water in the case ofb. to the desired concentration.

After conclusion of the tests, the lowest concentration in each case wasdetermined at which the compounds still caused 80-100% inhibition ormortality in comparison to untreated control tests (activity thresholdor minimum concentration).

We claim:
 1. A benzyloxyimino compound of formula I,

wherein X is N(COOCH₃)—OCH₃, C(COOCH₃)═CH—OCH₃, C(COOCH₃)═N—OCH₃,C(CONHCH₃)═N—OCH₃ or C(COOCH₃)═CH—CH₃; Y is hydrogen, halogen,C₁-C₄-alkyl, C₁-C₄-halolakyl or C₁-C₄-alkoxy; Z is oxygen or CH₂; R¹ ishalogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxy; R² is hydrogen;R³ is hydrogen; R⁴ is C₁-C₄-alkyl or phenyl which is unsubstituted orcarries from one to three substituents from the following group:halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy orC(R^(b))═N—OR^(c), wherein R^(b) is hydrogen or C₁-C₄-alkyl and R^(c) isC₁-C₄-alkyl, C₃-C₄-alkenyl or C₃-C₄-alkynyl, wherein Z is not CH₂ if Xis C(COOCH₃)═CH—OCH₃ or C(COOCH₃)═N—OCH₃ and R⁴ is C₁-C₄-alkyl.
 2. Anoxime of formula II

wherein Z is oxygen; R¹ is halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl orC₁-C₄-alkoxy, R² is hydrogen, R³ is hydrogen, and R⁴ is C₁-C₄-alkyl orphenyl with or without substitution by 1-3 substituents from thefollowing group: halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy or C(R^(b))═N—OR^(c), wherein R^(b) is hydrogen orC₁-C₄-alkyl and R^(c) is C₁-C₄-alkyl, C₃-C₄-alkenyl or C₃-C₄-alkynyl. 3.The compound of formula I defined in claim 1, wherein R² and R³ are eachhydrogen.
 4. The compound of formula I defined in claim 1, wherein X isN(COOCH₃)—OCH₃.
 5. The compound of formula I defined in claim 1, whereinZ is oxygen, and R⁴ is phenyl which is unsubstituted or carries from oneto three substituents from the following group: halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C(R^(b))═N—OR^(c). 6.The oxime of formula II defined in claim 2, wherein R⁴ is phenyl whichis unsubstituted or carries from one to three substituents from thefollowing group: halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy or C(R^(b))═N—OR^(c).
 7. A benzyloxyimino compound offormula I,

wherein X is N(COOCH₃)—OCH₃; Y is hydrogen, halogen, C₁-C₄-alkyl,C₁-C₄-halolakyl or C₁-C₄-alkoxy; Z is oxygen or CH₂; R¹ is halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxy; R² is hydrogen orC₁-C₄-alkyl; R³ is hydrogen or C₁-C₄-alkyl; R⁴ is C₁-C₄-alkyl or phenylwhich is unsubstituted or carries from one to three substituents fromthe following group: halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C(R^(b))═N—OR^(c), wherein R^(b) ishydrogen or C₁-C₄-alkyl and R^(c) is C₁-C₄-alkyl, C₃-C₄-alkenyl orC₃-C₄-alkynyl.
 8. A composition suitable for controlling animal pests orharmful fungi, comprising a solid or liquid carrier and the compound offormula I defined in claim
 1. 9. The composition defined in claim 8,wherein X of the compound of formula I is N(COOCH₃)—OCH₃.
 10. Thecomposition defined in claim 8, wherein Z of the compound of formula Iis oxygen, and R⁴ is phenyl which is unsubstituted or carries from oneto three substituents from the following group: halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C(R^(b))═N—OR^(c).11. A composition suitable for controlling animal pests or harmfulfungi, comprising a solid or liquid carrier and the compound of formulaI defined in claim
 7. 12. A method for controlling harmful fungi, whichcomprises treating the fungi or the materials, plants, the soil or seedsto be protected against attack by fungi with an effective amount of thecompound of formula I defined in claim
 1. 13. A method for controllinganimal pests, which comprises treating the animal pests or thematerials, plants, the soil or seeds to be protected against them withan effective amount of the compound of formula I defined in claim
 1. 14.The method of claim 12, wherein X of the compound of formula I isN(COOCH₃)—OCH₃.
 15. The method of claim 13, wherein X of the compound offormula I is N(COOCH₃)—OCH₃.
 16. The method of claim 12, wherein Z ofthe compound of formula I is oxygen, and R⁴ is phenyl which isunsubstituted or carries from one to three substituents from thefollowing group: halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy or C(R^(b))═N—OR^(c).
 17. The method of claim 13,wherein Z of the compound of formula I is oxygen, and R⁴ is phenyl whichis unsubstituted or carries from one to three substituents from thefollowing group: halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy or C(R^(b))═N—OR^(c).
 18. A method for controllingharmful fungi, which comprises treating the fungi or materials, plants,soil or seeds to be protected against attack by fungi with an effectiveamount of the compound of formula I defined in claim
 7. 19. A method forcontrolling animal pests, which comprises treating the animal pests ormaterials, plants, soil or seeds to be protected against them with aneffective amount of the compound of formula I defined in claim
 7. 20. Aprocess for preparing the compound of formula I defined in claim 1,which comprises reacting an oxime of formula II

with a benzyl compound of formula III,

wherein L is a leaving group.
 21. A process for preparing the compoundof formula I defined in claim 1 wherein Z is oxygen, which comprisesreacting a benzyl compound of formula III with an oxime of formula IV

to give an oxime ether of formula V

which is subsequently converted by oxidation into the compound offormula I.